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[ CAS No. 133730-34-4 ] {[proInfo.proName]}

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Chemical Structure| 133730-34-4
Chemical Structure| 133730-34-4
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Product Details of [ 133730-34-4 ]

CAS No. :133730-34-4 MDL No. :MFCD01074590
Formula : C8H11BO4 Boiling Point : -
Linear Structure Formula :(C6H3)(OCH3)2B(OH)2 InChI Key :SQTUYFKNCCBFRR-UHFFFAOYSA-N
M.W : 181.98 Pubchem ID :2734341
Synonyms :

Calculated chemistry of [ 133730-34-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.25
TPSA : 58.92 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.77
Log Po/w (WLOGP) : -0.62
Log Po/w (MLOGP) : -0.25
Log Po/w (SILICOS-IT) : -0.74
Consensus Log Po/w : -0.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.6
Solubility : 4.6 mg/ml ; 0.0253 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 4.7 mg/ml ; 0.0258 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.54
Solubility : 5.21 mg/ml ; 0.0286 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.21

Safety of [ 133730-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 133730-34-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 133730-34-4 ]

[ 133730-34-4 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 133730-34-4 ]
  • [ 3153-72-8 ]
  • 2
  • [ 133730-34-4 ]
  • [ 203436-13-9 ]
  • 2-(2,4-dimethoxyphenyl)-6-(4-methoxybenzylamino)-9-isopropylpurine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis(mesityl)imidazolium chloride; In 1,4-dioxane; at 80℃; for 8h;Product distribution / selectivity; A 10 mL flame-dried Schlenk flask equipped with a magnetic stir bar was charged with 2-chloro-6-(4-methoxybenzylamino)-9-isopropylpurine (0.193 g, 0.5 mmol, 1.0 equiv), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (0.136 g, 0.75 mmol, 1.5 equiv), Pd2(dba)3 (0.0069 g, 0.0075 mmol, 0.015 equiv.), ligand 1 (0.0051 g, 0.015 mmol, 0.03 equiv.) and Cs2CO3 (0.326 g, 1.0 mmol, 2.0 equiv.). The Schlenk flask was evacuated and backfilled with argon and charged with anhydrous 1,4-dioxane (2.0 mL). The reaction was stirred under argon at 80 C. and monitored by TLC. When the reaction was complete after 8 hours, the solvent was removed in vacuo and the reaction crude was purified by flash column chromatography (3% methanol in dichloromethane) to afford desired 2-(2,4-dimethoxyphenyl)-6-(4-methoxybenzylamino)-9-isopropylpurine (207 mg, 96%). 1H NMR (400 MHz, CDCl3) δ1.59 (d, 6H, J=6.8 Hz), 3.79 (s, 3H), 3.84 (s, 3H), 3.85 (s, 3H), 4.87-4.96 (m, 3H), 6.14 (br, 1H), 6.57-6.60 (m, 2H), 6.85 (d, 2H, J=8.6 Hz), 7.34 (d, 2H, J=8.6 Hz), 7.73 (s, 1H), 7.78 (d, 1H, J=8.2 Hz); HRMS (MALDI-FTMS) [MH+] C24H28N5O3 434.2187, found: 434.2168.
  • 3
  • [ 3934-20-1 ]
  • [ 133730-34-4 ]
  • 2-chloro-4-(2,4-dimethoxyphenyl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With palladium diacetate; potassium carbonate; triphenylphosphine; In water; isopropyl alcohol; at 80 - 90℃; for 20h;Inert atmosphere; To a 100 mL flask containing 2,4-dichloropyrimidine (9.8 g, 65.7 mmol) in isopropyl alcohol (80 mL) was added <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (10 g, 54.9 mmol), palladium acetate (0.62 g, 2.7 mmol) and triphenyl phosphine (3.48 g, 13.2 mmol). Potassium carbonate (1 1 .38 g, 82.4 mmol) was dissolved in water (25 mL) and was added to the reaction mixture. The reaction mixture was stirred under nitrogen at 80-90 C for 20 h. The reaction mixture was cooled to room temperature and was concentrated. The residue was partitioned between ethyl acetate (2 x 100 mL) and water (50 mL). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was evaporated to obtain the title compound, which was further purified by column chromatography to obtain the title compound. Yield: 10 g (61 %); 1 H NMR (300 MHz, DMSO-d6):5 8.68 (d, 1 H), 8.04 (m, 2H), 6.74 (m, 2H), 3.92 (s, 3H), 3.88 (s, 3H); MS (ES+): 251 (M+1 ).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 4h;Inert atmosphere; General procedure: 1.50 g (10.00 mmol) 2,4-dichloropyrimidine was dissolved in 60 ml degassed 1,2-dimethoxyethane under inert atmosphere and stirred for 10 min. 0.23 g (0.20 mmol) tetrakis(triphenylphosphine)palladium(0) was added to the solution and argon was bubbled through the solution for 30 minutes. 1.67 g (11.00 mmol) 2-methoxyphenylboronic acid and the solution of 3.18 g (30.00 mmol) sodium carbonate in 15 ml water were added to the solution, and the mixture was stirred under argon at reflux temperature for 4 hours. The reaction mixture was cooled down to room temperature, and diluted with 150 ml water. The product was extracted three times with 150 ml ethyl acetate. The organic layers were separated, combined, washed with saturated sodium chloride solution and dried over magnesium sulphate. The solvent was removed under reduced pressure. The residual was crystallized from acetonitrile.
  • 4
  • [ 6451-86-1 ]
  • [ 133730-34-4 ]
  • [ 796843-31-7 ]
  • 5
  • [ 17715-69-4 ]
  • [ 133730-34-4 ]
YieldReaction ConditionsOperation in experiment
610.2 mg With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20℃; for 2.66667h;Inert atmosphere; 576 μl of 1-bromo-2,4-dimethoxybenzene was dissolved in 5.8 ml of tetrahydrofuran and 3 ml of a 1.6 mol/l solution of n-butyllithium in hexane was added dropwise under an argon atmosphere at -78 C. Then, 1.1 ml of triisopropyl borate was added, followed by stirring at -78 C. for 40 minutes and then stirring at room temperature for 2 hours. To the reaction mixture were added 40 ml of water and 1 ml of 5N-hydrochloric acid, followed by extracting with 50 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, subsequently the solvent was distilled off under reduced pressure, and purification using silica gel column chromatography (hexane:ethyl acetate=2:1) afforded 610.2 mg of the title compound. [0296] 1H-NMR (CDCl3); δ (ppm) 3.85 (3H, s), 3.89 (3H, s), 5.81 (2H, s), 6.46 (1H, s), 6.56 (1H, dd, J=2.0, 8.4 Hz), 7.77 (1H, d, J=8.4 Hz).
610.2 mg With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20℃; for 2.66667h;Inert atmosphere; 576 μl of 1-bromo-2,4-dimethoxybenzene was dissolved in 5.8 ml of tetrahydrofuran and 3 ml of a 1.6 mol/l solution of n-butyllithium in hexane was added dropwise under an argon atmosphere at -78C. Then, 1.1 ml of triisopropyl borate was added, followed by stirring at -78C for 40 minutes and then stirring at room temperature for 2 hours. To the reaction mixture were added 40 ml of water and 1 ml of 5N-hydrochloric acid, followed by extracting with 50 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, subsequently the solvent was distilled off under reduced pressure, and purification using silica gel column chromatography (hexane:ethyl acetate=2:1) afforded 610.2 mg of the title compound. 1H-NMR (CDCl3); δ (ppm) 3.85 (3H, s), 3.89 (3H, s), 5.81 (2H, s), 6.46 (1H, s), 6.56 (1H, dd, J=2.0, 8.4Hz), 7.77 (1H, d, J=8.4Hz).
  • 6
  • [ 614-76-6 ]
  • [ 133730-34-4 ]
  • N-(2',4'-dimethoxy-[1,1'-biphenyl]-2-yl)acetamide [ No CAS ]
  • 8
  • [5-(4-bromophenyl)-1H-pyrazol-3-yl]phenylamine [ No CAS ]
  • [ 133730-34-4 ]
  • [5-(2',4'-dimethoxybiphenyl-4-yl)-1H-pyrazol-3-yl]phenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With water; potassium carbonate; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 90℃; To a solution of the bromide (above) in dioxane (10 mL) was added 2,4- dimethoxyboronic acid (371 mg, 2.0 MMOL), potassium carbonate (352 mg, 2.5 MMOL), triethylamine (0.4 mL, 2.5 MMOL) and water (0.3 mL). The system was vacuum flushed with nitrogen, then dichloro-di-triphenylphosphoro palladium catalyst (60 mg, 5 mol%) was added. Reaction heated at 90C overnight. Purified by column using ethyl acetate: hexanes 1: 2 isolating the title compound as an amber oil (46 mg, 7%). H NMR (CD30D) 8 : 3.70 (3H, s), 3.74 (3H, s), 6.20 (1H, s), 6.54 (2H, bm), 6.69 (1H, bs), 7.11 (6H, BM), 7.44 (2H, d, J=7.83 Hz), 7.57 (2H, m). MS (APCI POSITIVE) 372.2.
  • 9
  • [ 99-90-1 ]
  • [ 133730-34-4 ]
  • [ 178055-99-7 ]
YieldReaction ConditionsOperation in experiment
82% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 17h;Heating / reflux; Into a solution of 4-bromoacetophenone (7 g, 35.4 MMOL) in DME (135 mL), were added 2, 4-dimethoxyphenyl boronic acid (8.4 g, 46.2 MMOL), Pd (PPh3) 4 (2.03 g, 1.8 MMOL), and 37 mL OF 2M NA2CO3 1-under N2. The mixture was REFLUXED with stirring for 17 hours and allowed to cool to room temperature. The reaction solution was diluted with ethyl acetate. The organic layer was separated, washed twice with water, and dried over NA2SO4. Solvent removal under reduced pressure gave a sticky residue. The residue was purified using silica gel column chromatography with ethyl acetate: hexanes (1: 4) eluents to afford 1- (2 , 4'- dimethoxy-1, 1'-biphenyl-4-yl) ethanone as a white solid. Yield: 7.45 G (82%). H NMR (DMSO-d6) 8 7.95 (d, 2H), 7.58 (d, 2H), 7.28 (d, 1H), 6.65 (t, 2H), 3.81 (s, 3H), 3.77 (s, 3H), 2.58 (s, 3H)
  • 10
  • [ 696-62-8 ]
  • [ 133730-34-4 ]
  • 2,4,4'-trimethoxy-biphenyl [ No CAS ]
  • 11
  • [ 619-42-1 ]
  • [ 133730-34-4 ]
  • [ 208652-71-5 ]
YieldReaction ConditionsOperation in experiment
With tetrabutylammomium bromide; potassium carbonate;palladium diacetate; In water; at 80℃; for 0.666667h; To a 100 mL flask, methyl 4-bromobenzoate (1.42 g), <strong>[133730-34-4]2,4-dimethoxybenzeneboronic acid</strong> (1.3 g), Pd (OAc)2 (100 mg), K2CO3 (1.9 g) and tetrabutylammonium bromide (3.54 g) were added. The flask was flushed with N2 and sealed with a rubber septum. Water (50 mL) was added with a syringe, and the resulting suspension was stirred and deoxygenated with N2 at room temperature. The mixture was stirred and heated for 40 min. at 80 C. under N2, cooled to room temperature, and acidified to pH 1 with concentrated HCl. The precipitate (Pd) was filtered off and washed with EtOAc. The filtrate was extracted with EtOAc, washed with saturated brine, dried over anhydrous Na2SO4 and concentrated to give crude product 23.
  • 12
  • C23H23BrN3O3Pol [ No CAS ]
  • [ 133730-34-4 ]
  • C31H32N3O5Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In 1,4-dioxane; at 80℃; Suzuki reaction according to G. C. Fu et al., Angew. Chem. 1998, 110, 3586-3587:1 gram of resin bound 3-(3-aminomethyl-cyclohexylmethyl)-2-(4-bromophenyl)-3H-quinazolin-4-one is suspended in 10 ml of 1,4-dioxane. The reaction is then treated with 1.62 mmol Cs2CO3, 1.62 mmol of 2,4-dimethoxyphenyl boronic acid and 10 mol % ([Pd2(dba)3]+P(tert-Bu)3). The reaction is then allowed to shake at 80 until conversion is complete. After cooling the reaction mixture, it is worked up as is customary.
  • 13
  • [ 872857-72-2 ]
  • [ 133730-34-4 ]
  • [ 872857-74-4 ]
YieldReaction ConditionsOperation in experiment
71% A solution of compound 5 (4.0 g, 0.014 mol) and 2,4-dimethoxy benzeneboronic acid (3.0 g, 0.016 mol), KF (4.0 g, 0.069 mol) and Pd(PPh3)4 (0.75 g, 0.0007 mol) was heated at reflux in dioxane (100 mL) overnight. The crude reaction mixture (after cooling to room temperature) was treated with a 50% NaOH (30 mL, aqueous) solution and stirred at room temperature until TLC indicated hydrolysis of the enol acetate was complete. The basic solution was neutralized with 2 N HCl and the dioxane removed under reduced pressure. The resultant mixture was extracted with ethyl acetate, washed with NaHCO3, brine and dried over MgSO4. Filtration, concentration and chromatography on silica gel (EtOAc/hexanes-gradient) yielded 7 as a white solid (2.9 g, 71%): Mp=116-118 C.; 1H NMR (CDCl3) δ 8.05 (d, 1H, J=8.7 Hz), 6.96 (d, 1H, J=8.2 Hz), 6.82 (dd, 1H, J=8.6 Hz, 2.1 Hz), 6.71 (s, 1H), 6.47 (d, 1H, J=2.1 Hz), 6.42 (d, 1H, J=8.2 Hz), 3.93 (dd, 1H, J=11.7 Hz, 4.6 Hz), 3.85 (s, 3H), 3.78 (s, 3H), 3.72 (s, 3H), 3.23-3.00 (m, 1H), 2.99-2.88 (m, 1H), 2.47-2.35 (m, 1H), 2.25-2.17 (m, 1H).
  • 14
  • [ 196103-66-9 ]
  • [ 133730-34-4 ]
  • [ 874968-78-2 ]
YieldReaction ConditionsOperation in experiment
60% With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6h;Heating / reflux; Methyl 3-(2,4-DimethoxyphenyI)-4-nitrobenzoate; To a deoxygenated mixture of 2,4-dimethoxyphenyl boronic acid (2.24g, 12.3 mmol), 5-(methoxycarbonyl)-2-nitrophenyltrifluoromethanesulfonate (2.77 g, 8.40 mmol), and potassium phosphate (1.32 g, 6.21mmol) in ethylene glycol dimethyl ether (70 mL) was added tetrakis(triphenylphosphine)palladium(O) (738 mg, 0.639mmol). The reaction was heated atreflux for 6 hours under inert atmosphere, cooled to ambient temperature, and filteredthrough a bed of Celite. The bed was rinsed with several volumes of ethyl acetate. Thefiltrate was washed successively with 1M sodium hydroxide solution (2 x 100 mL), 1MHC1 (2 x 100 mL), water (100 mL), and saturated sodium chloride solution (100 mL),dried over sodium sulfate, filtered, and concentrated in vacua to a brown residue. Thecrude material was purified by silica gel chromatography (dichloromethane : hexanes (1: 1)) to afford a bright yellow solid (1.60 g, 60%).
  • 15
  • [ 544678-59-3 ]
  • [ 133730-34-4 ]
  • [ 544678-39-9 ]
YieldReaction ConditionsOperation in experiment
69% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; 1,2-dimethoxyethane; dimethyl sulfoxide; Example 8 6-{2-[2-(2,4-Dimethoxy-phenyl)-quinazolin-4-ylamino]-ethylamino}-nicotinonitrile (Compound I-185) A mixture of 6-[2-(2-Chloro-quinazolin-4-ylamino)-ethylamino]-nicotinonitrile (65 mg, 0.2 mmol), <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (55 mg, 0.3 mmol), tetrakis(triphenylphosphine)palladium (2 mg) and aqueous saturated NaHCO3 (0.5 ml) in 1,2-dimethoxyethane (3 ml) was stirred at 110 C. under nitrogen for 14 h. The reaction mixture was concentrated. The residue was dissolved in a mixture of DMSO and MeOH and purified by reverse-phase HPLC. The title compound was obtained as a white solid (76 mg, 69%). 1H NMR (500 MHz, DMSO(d6)): δ13.20 (s, 1H), 10.20 (m, 1H), 8.38 (d, 2H), 8.00 (m, 2H), 7.82 (m, 1H), 7.78 (d, 2H), 7.72 (t, 1H), 6.80 (s, 1H), 6.70 (d, 1H), 3.90 (m, 7H), 3.83 (s, 3H). FIA-MS: (ES-) m/e=425.3 (M-H), (ES+) m/e=427.2 (M+H).
  • 16
  • [ 133730-34-4 ]
  • [ 586-78-7 ]
  • [ 860478-21-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 24h; To a degassed solution of 4-bromonitrobenzene (24.37 g, 120.63 mmol) and <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (20.95 g,115.07 mmol) in 600 mL of 1,4-dioxane was added tetrakis(triphenylphosphine) palladium(0) (8.0g, 7 mmol) followed by a solution of potassium carbonate (17.06 g, 124.3 mmol) in120 mL of water. The reaction was stirred with heating at 80C for 24 h, cooled, filtered andconcentrated. The resultant material was partitioned between ethyl acetate and water. Theorganic layer was washed with saturated NaHCOs, brine, dried over MgSCU andconcentrated. The resultant solid material was re-crystallized from hexane-ethyl acetate toafford 23.56 g of the desired product 28 as yellow crystals. JH NMR (dmso-d6): 5 8.22 (d,J=8.8 Hz, 2H), 7.73 (d, J=8.8 Hz, 2H), 7.34 (d, J=8.5 Hz, 1H), 6.71 (d, J=2.2 Hz, 1H), 6.67(dd, J=8.5, 2.2 Hz, 1H), 3.82 (s, 3H), 3.80 (s, 3H).
  • 17
  • [ 942438-82-6 ]
  • [ 133730-34-4 ]
  • 4-amino-8-(2,4-dimethoxy-phenyl)-7-fluoro-N-propylcinnoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 80℃; for 18.1667h; EXAMPLE 78 4-Amino-8-(2,4-dimethoxyphenyl)-7-fluoro-N-propylcinnoline-3-carboxamide Synthetic Scheme for Making Compound 78: A 2 L, 3-necked flask equipped with a mechanical stirrer was charged with 4-amino7-fluoro-8-iodo-N-propylcinnoline-3-carboxamide (40.5 g, 108.2 mmol), DME (700 mL, anhydrous), and ethanol (200 mL, absolute). A nitrogen dispersion tube was fitted into the suspension and the mixture was stirred until a solution was obtained. Water (300 mL) and PdCl2(PPh3)2 (7.6 g, 10 mol %) were added. After 5 minutes, 2,4-dimethoxyphenyl boronic acid (39.4 g, 216.5 mmol) was added followed by cesium carbonate (70.3 g, 216.5 mmol). Nitrogen was bubbled through the suspension for 5 minutes. The mixture was heated to approximately 80 C. Additional 7:3:2 DME:H2O:EtOH (340 mL) was added as the reflux started. The reaction was refluxed 18 hours and then cooled to room temperature, diluted with ethyl acetate (1.5 L), and washed with water (3×500 mL). The aqueous layers were extracted with ethyl acetate (3×150 mL). The combined organic layers were stirred for 1 hour with 40 g of DARCO, dried over sodium sulfate, and filtered through Celite. The solids were washed with 5% methanol in chloroform (3×200 mL) and the filtrates concentrated to a dark semisolid. This was taken up in 200 mL 1% methanol in chloroform and warmed to solubilize the material. The solution was divided into two portions. Each portion was filtered through Whatman fluted filter paper onto a 330 g silica gel column and eluted with 5% ethyl acetate in dichloromethane. (Note: Some solid catalyst appeared to be removed via the filter paper.) The purest fractions from each column were combined in 5-10% ethyl acetate in dichloromethane. The solution was concentrated to approximately 200 mL, diluted with hexane (200 mL), and let stand at room temperature overnight. The resulting solids were isolated by filtration, washed with ether (3 times), and dried under vacuum at room temperature to afford the desired product (26.4 g, 63%). 1H NMR (500.333 MHz, CDCl3) δ 8.51 (bs, 1H), 7.86 (dd, J=9.4, 5.2 Hz, 1H), 7.50 (t, J=8.8 Hz, 1H), 7.27 (d, J=9.2, 1H), 6.66 (dd, J=8.2, 2.3 Hz, 1H), 6.63 (d, J=2.3 Hz, 1H), 3.87 (s, 3H), 3.71 (s, 3H), 3.44 (q, J=6.7 Hz, 2H), 1.64 (sextet, J=7.3 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H). MS APCI, m/z=385 (M+H). HPLC: 2.61 min.
63% With nitrogen; caesium carbonate;PdCl2(PPh3)2; In 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; water; ethyl acetate; EXAMPLE 78 4-Amino-8-(2,4-dimethoxyphenyl)-7-fluoro-N-propylcinnoline-3-carboxamide A 2 L, 3-necked flask equipped with a mechanical stirrer was charged with 4-amino7-fluoro-8-iodo-N-propylcinnoline-3-carboxamide (40.5 g, 108.2 mmol), DME (700 mL, anhydrous), and ethanol (200 mL, absolute). A nitrogen dispersion tube was fitted into the suspension and the mixture was stirred until a solution was obtained. Water (300 mL) and PdCl2(PPh3)2 (7.6 g, 10 mol %) were added. After 5 minutes, 2,4-dimethoxyphenyl boronic acid (39.4 g, 216.5 mmol) was added followed by cesium carbonate (70.3 g, 216.5 mmol). Nitrogen was bubbled through the suspension for 5 minutes. The mixture was heated to approximately 80 C. Additional 7:3:2 DME:H2O:EtOH (340 mL) was added as the reflux started. The reaction was refluxed 18 hours and then cooled to room temperature, diluted with ethyl acetate (1.5 L), and washed with water (3*500 mL). The aqueous layers were extracted with ethyl acetate (3*150 mL). The combined organic layers were stirred for 1 hour with 40 g of DARCO, dried over sodium sulfate, and filtered through Celite. The solids were washed with 5% methanol in chloroform (3*200 mL) and the filtrates concentrated to a dark semisolid. This was taken up in 200 mL 1% methanol in chloroform and warmed to solubilize the material. The solution was divided into two portions. Each portion was filtered through Whatman fluted filter paper onto a 330 g silica gel column and eluted with 5% ethyl acetate in dichloromethane. (Note: Some solid catalyst appeared to be removed via the filter paper.) The purest fractions from each column were combined in 5-10% ethyl acetate in dichloromethane. The solution was concentrated to approximately 200 mL, diluted with hexane (200 mL), and let stand at room temperature overnight. The resulting solids were isolated by filtration, washed with ether (3 times), and dried under vacuum at room temperature to afford the desired product (26.4 g, 63%). 1H NMR (500.333 MHz, CDCl3) δ 8.51 (bs, 1H), 7.86 (dd, J=9.4, 5.2 Hz, 1H), 7.50 (t, J=8.8 Hz, 1H), 7.27 (d, J=9.2, 1H), 6.66 (dd, J=8.2, 2.3 Hz, 1H), 6.63 (d, J=2.3 Hz, 1H), 3.87 (s, 3H), 3.71 (s, 3H), 3.44 (q, J=6.7 Hz, 2H), 1.64 (sextet, J=7.3 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H). MS APCI, m/z=385 (M+H). HPLC: 2.61 min.
  • 18
  • [ 99-91-2 ]
  • [ 133730-34-4 ]
  • [ 178055-99-7 ]
  • 19
  • [ 523-27-3 ]
  • [ 133730-34-4 ]
  • [ 1021540-42-0 ]
YieldReaction ConditionsOperation in experiment
32% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 110℃; Add 9,10-dibromoanthracene and <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> at a molar ratio of 1:2 into the round bottom flask,Then add anhydrous sodium carbonate and catalyst [1,1’-bis(diphenylphosphino)ferrocene] palladium dichloride 10% mol,Use 1,4-dioxane and water volume ratio 4:1 as solvent,Reflux overnight at 110C, evaporate the solvent after the reaction is complete,Extract with water and dichloromethane, dry with anhydrous sodium sulfate,The mixture was separated through a silica gel column to obtain 9,10-bis(2,4-dimethoxyphenyl)anthracene as a white solid.The yield was 32%.
  • 20
  • 9-amino-5-bromo-2-cyclobutyl-6-fluoro-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one [ No CAS ]
  • [ 133730-34-4 ]
  • [ 1093948-57-2 ]
YieldReaction ConditionsOperation in experiment
60% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 20 - 150℃; for 0.333333 - 1h;Microwave irradiation; EXAMPLE 1009-Amino-2-cyclobutyl-5-(2,4-dimethoxyphenyl)-6-fluoro-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-oneUsing Method F, 9-amino-5-bromo-2-cyclobutyl-6-fluoro-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (150 mg, 0.43 mmol), and 2,4-Dimethoxyphenylboronic acid (234 mg, 1.29 mmol) were reacted to afford the title compound as a white solid (104 mg, 60% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.56-8.16 (m, 1H), 7.67 (br, 2H), 7.39 (t, J=9 Hz, 1H), 7.08 (d, J=9 Hz, 1H), 6.70-6.67 (m, 2H), 4.71 (m, 1H), 4.38 (s, 2H), 3.84 (s, 3H), 3.64 (s, 3H), 2.30 (m, 2H), 2.11 (m, 2H), 1.67 (m, 2H). MS APCI, m/z=408 (M+H).; Method F: The quinoline-halide, arylboronic acid (typically 2-3 molar equivalents), cesium carbonate (2-3 molar equivalents) and bis(triphenylphosphine)palladium(II) dichloride (0.05 molar equivalents) were placed in a microwave reaction vessel and dissolved in 7:3:2 (v/v/v) 1,2-dimethoxyethane: water: ethanol (10 mL/mmol cinnoline-halide) at ambient temperature. The reaction vessel was capped, the head-space purged with dry nitrogen and the stirred mixture was heated on a Biotage Optimizer (300 W) microwave system maintaining a reaction temperature of 150 C. for 20-60 minutes, reaction pressures of 7 bar were typically observed. The reaction was then cooled to ambient temperature and extracted with ethyl acetate. The residue from the organic extracts was purified by flash chromatography on silica gel eluting with increasingly polar gradient of ethyl acetate in hexanes to afford the desired compound.
  • 21
  • [ 666252-87-5 ]
  • [ 133730-34-4 ]
  • [ 355834-36-5 ]
YieldReaction ConditionsOperation in experiment
A MIXED SOLUTION OF 5-BROMO- [N- (L-ETHYL) PROPYL] -3, 6-DIMETHYLPYRAZINE-2-AMINE] (0.40 g; 1.47 mmol) and tetrakis (triphenylphosphine) palladium [(0)] (33 mg; 2 mol%) in ethyleneglycol dimethyl ether (8 mL) is stirred at room temperature for 15 minutes, after which <strong>[133730-34-4]2,4-dimethoxybenzeneboronic acid</strong> (1.76 mmol) and an aqueous solution of sodium carbonate (1. OM, 4 mL) are added sequentially. The mixture is heated to 75 C with stirring for 1.5 hours, then diluted with [0.] IN sodium hydroxide and extracted twice with 1: 1 hexane- ethyl ether. Combined extracts are dried (sodium sulfate), filtered, concentrated, and chromatographed on silica (4: 1 to 1: 1 hexane-EtOAc) to give the title compound (0.50 g): 1H NMR (CDC13,400 MHz) [8] 0.95 (t, 6H), 1.6 (m, 4H), 2.2 (s, 3H), 2.4 (s, 3H), 3.75 (s, 3H), 3.85 (s, 3H), 3.95 (br d, 1H), 4.1 (br q, 1H), 6.5 (s, 1H), 6.55 (d, 1H) 7.2 [(D,] 1H) ; MS (CI) 330.
  • 22
  • [ 6942-36-5 ]
  • [ 133730-34-4 ]
  • [ 1026777-98-9 ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80℃; Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No.1-1-(1)) A mixture of <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (25.0 g, 137 mmol), methyl 2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g, 274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g, 6.85 mmol) was suspended in N,N-dimethylformamide (450 mL), and then the suspension was stirred under argon atmosphere at 80C overnight. After cooling down, ethyl acetate (200 mL), diethylether (400 mL) and water (1000 mL) were added thereto and the mixture was separated into a water phase and an organic layer. The water layer was extracted with a mixed solvent of ethyl acetate (150 mL) - diethylether (150 mL) (twice). The combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound as a brown oil. (Quantitative)
100% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; Reference Example 1; 5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1)Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No. 1-(1))A mixture of <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (25.0 g, 137 mmol), methyl 2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g, 274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g, 6.85 mmol) was suspended in N,N-dimethylformamide (450 mL), and then the suspension was stirred under argon atmosphere at 80 C. overnight. After cooling down, ethyl acetate (200 mL), diethylether (400 mL) and water (1000 mL) were added thereto and the mixture was separated into a water phase and an organic layer. The water layer was extracted with a mixed solvent of ethyl acetate (150 mL)-diethylether (150 mL) (twice). The combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound as a brown oil. (Quantitative)
40% With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In water; at 150℃; for 0.166667h;Microwave irradiation; Commercially available <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (0.182 g, 1.00 mmol), sodium carbonate (0.318 g, 3.00 mmol), aryl bromide 4 (0.261 g, 1.00 mmol), palladium (II) acetate (0.0009 g, 0.004 mmol), tetra-n-butylammonium bromide (0.322 g, 1.00 mmol) and 10 mL of water were added to a microwave vial. The sealed vial was heated in the microwave for 10 min at 150 C. The reaction was then allowed to cool to room temperature, diluted with 100 mL of water, and extracted 2x with ether. Combined ether extracts were then washed with brine and dried with MgSO4. The solvents were removed under reduced pressure. A yellow oil was isolated by column chromatography (0.6318 g, 40%). 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J=2.2 Hz, 1 H), 8.34 (dd, J=8.3, 2.5 Hz, 1 H), 7.49 (d, J=8.5 Hz, 1 H), 7.20 (d, J=8.5 Hz, 1 H), 6.61 (dd, J=8.4, 2.4 Hz, 1 H), 6.49 (d, J=2.2 Hz, 1 H), 3.87 (s, 3 H), 3.76 (s, 3 H), 3.71 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 166.85, 161.67, 156.92, 146.31, 145.16, 132.90, 132.51, 130.41, 125.82, 124.67, 121.06, 104.82, 98.42, 55.45, 55.18, 52.26. FT-IR (thin film, cm-1): 1734.34, 1609.70, 1523.04, 1349.12. TOF-MS (ESI, [M+H]+) calculated for C16H16NO6 318.0972; found 318.0952
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