887707-21-3

To a solution of 6-chloro-5-methylnicotinaldehyde (3.20 g, 20.7 mmol) in methanol (22 mL) was slowly added sodium borohydride (863 mg, 22.7 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, saturated aqueous ammonium chloride solution (20 mL) was added and the mixture continued to be stirred for 0.5 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was washed with water (50 mL) and extracted with dichloromethane (50 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (eluent ratio of petroleum ether/ethyl acetate=2/1) to afford the target product (6-chloro-5-methylpyridin-3-yl)methanol (3.2 g, 88% yield) as a light yellow solid.1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.56 (s, 1H), 4.65 (s 2H), 2.33 (s, 3H).

[1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 154 - 165
[2] Patent: WO2006/114213, 2006, A1. Location in patent: Page/Page column 30