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With methanol; sodium tetrahydroborate In dichloromethane at 0 - 20℃; for 18 h;
To a solution of 5-chloro-nicotinic acid methyl ester (17.2 g, 101 mmol) in methanol (230 mL) and DCM (230 mL) at 0° C. was added sodium borohydride (16.4 g, 434 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion, the reaction mixture was concentrated under reduced pressure, diluted with water (300 mL) and extracted with AcOEt (3×300 mL). The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford (5-chloro-pyridin-3-yl)-methanol (7.8 g, 54percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.45-8.52 (m, 2H), 7.83 (s, 1H), 5.45 (t, J=5.8 Hz, 1H), 4.55 (t, J=5.7 Hz, 2H). MS m/z 144.1
With methanol; sodium tetrahydroborate; In dichloromethane; at 0 - 20℃; for 18h;
To a solution of 5-chloro-nicotinic acid methyl ester (17.2 g, 101 mmol) in methanol (230 mL) and DCM (230 mL) at 0 C. was added sodium borohydride (16.4 g, 434 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion, the reaction mixture was concentrated under reduced pressure, diluted with water (300 mL) and extracted with AcOEt (3×300 mL). The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was then purified by silica gel chromatography to afford (5-chloro-pyridin-3-yl)-methanol (7.8 g, 54%). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.45-8.52 (m, 2H), 7.83 (s, 1H), 5.45 (t, J=5.8 Hz, 1H), 4.55 (t, J=5.7 Hz, 2H). MS m/z 144.1
With methanol; sodium tetrahydroborate; In dichloromethane; at 20℃; for 18h;
Sodium borohydride (790 mg, 20.9 mmol) was added to a solution of crude methyl 5-chloronicotinate (-6.35 mmol) in methanol (10 mL) and CH2CI2 (10 mL). After 18 h at room temperature, the reaction mixture was concentrated in vacuo. Water (50 mL) was added and the mixture was extracted with CH2CI2 (3x50 mL).The organic phase was dried (MgStheta4), filtered and concentrated in vacuo. . Purification of the crude residue by chromatography on 40 g silica gel (hexanes ? EtOAc, gradient) afforded 510 mg (56% over two steps) of(5-chloropyridin-3-yl)methanol.
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