5-Bromo-3-Methoxy-Pyridine2-Carbonitrile synthesis
- Product Name:5-Bromo-3-Methoxy-Pyridine2-Carbonitrile
- CAS Number:36057-46-2
- Molecular formula:C7H5BrN2O
- Molecular Weight:213.03
886373-28-0
124-41-4
36057-46-2
Sodium methanolate (2.68 g, 49.59 mmol) was added to a solution of 5-bromo-3-fluoropyridine-2-carbonitrile (2.00 g, 9.93 mmol) in tetrahydrofuran (THF, 80 mL) at room temperature. The reaction mixture was stirred at 70 °C for 3 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with a 3 M solution of HCl. The reaction mixture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 5-bromo-3-methoxypyridine-2-carbonitrile as a brown solid (2.00 g, 95% yield). Mass spectrum (MS): m/z = 213.0 [M + H]+.
67-56-1
781 suppliers
$7.29/5ml-f
573675-25-9
284 suppliers
$13.00/5g
36057-46-2
68 suppliers
$195.00/0.5 G
Yield: 78%
Reaction Conditions:
with sodium methylate for 8 h;Reflux;
Steps:
(a) 5-Bromo-3-methoxy-pyridine-2-carbonitrile
To a solution of 5-bromo-3-nitro-pyridine-2-carbo-nitrile (2 g, 8.8 mmol) in MeOH (25 ml), 0.5 M NaOMe (in MeOH, 15 ml) was added at room temperature. The reaction mixture was heated to reflux and stirred for 8 hours at this temperature. After the reaction completion, the reaction mixture was concentrated under reduced pressure. The residue was purified via column chromatography (Ethyl acetate : n-Hexane = 1 : 4) and the target compound of 1.46 g was obtained. (78% yield) 1H NMR (300 MHz, CDCl3): δ 8.318 (d, J= 1.5Hz, 1H), 7.523 (d, J= 1.5Hz, 1H), 3.973 (s, 3H), MS: m/z 215 [M+1]
References:
Hong, Yong Rae;Kim, Hyun Tae;Ro, Seonggu;Cho, Joong Myung;Lee, Sang Hwi;Kim, In Su;Jung, Young Hoon [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 14,p. 3142 - 3145] Location in patent:supporting information
886373-28-0
167 suppliers
$8.00/250mg
124-41-4
727 suppliers
$12.00/25g
36057-46-2
68 suppliers
$195.00/0.5 G
573675-25-9
284 suppliers
$13.00/5g
124-41-4
727 suppliers
$12.00/25g
36057-46-2
68 suppliers
$195.00/0.5 G