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ChemicalBook CAS DataBase List 5-BENZYLOXY-1-BOC-INDOLE-2-BORONIC ACID
850568-62-6

5-BENZYLOXY-1-BOC-INDOLE-2-BORONIC ACID synthesis

4synthesis methods
-

Yield:850568-62-6 100%

Reaction Conditions:

with Triisopropyl borate in tetrahydrofuran;n-heptane;ethylbenzene; for 2.41667 h;Cooling with ice;

Steps:

56.b

To a solution of 1,1 -dimethylethyl 5-[(phenylmethyl)oxy]-lH-indole-l -carboxylate(1.76 g, 4.8 mmol) in tetrahydrofuran (10 mL) was added triisopropyl borate (2.2 mL, 9.5 mmol). The solution was stirred in an ice-water bath under a nitrogen atmosphere and lithium diisopropylamide (2 M in heptane/tetrahydrofuran/ethylbenzene) (4 mL, 8 mmol) was added, portionwise, over 20 min. The reaction mixture was swirled to facilitate mixing, then stirred with cooling for 45 m. Lithium diisopropylamide (2 M in heptane/tetrahydrofuran/ethylbenzene) (0.8 mL, 1.6 mmol) was added to the reaction mixture over a 5-min period. The cold reaction mixture was swirled to facilitate mixing, then stirred for 75 min. Hydrochloric acid (1 N) (50 mL) was added to the reaction mixture and the aqueous mixture was extracted with ethyl acetate. The organic extract was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give 2.03 (100%) of {l-{[(l,l-dimethylethyl)oxy]carbonyl}-5-[(phenylmethyl)oxy]-l/f-indol- 2-yl}boronic acid as a tan solid. 1U NMR (400 MHz, DMSO-J6): δ 8.15 (s, 2H), 7.93 (d, J = 9 Hz, IH), 7.44 (d, 2H), 7.37 (m, 2H), 7.30 (m, IH), 7.15 (d, J = 2 Hz, IH), 6.94 (dd, J = 9, 2 Hz, IH), 6.51 (s, IH), 5.09 (s, 2H), 1.56 (s, 9H).

References:

WO2009/5998,2009,A1 Location in patent:Page/Page column 256-257

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