Step 2: Synthesis of 3-(bromomethyl)-2-methoxypyridine (Int-37)
To a dichloromethane solution (10 mL) of (2-methoxypyridin-3-yl)methanol (811 mg, 5.8 mmol) and N-bromosuccinimide (1.24 g, 7.0 mmol), triphenylphosphine (1.8 g, 7.0 mmol) was added at room temperature and the mixture was stirred for 2 hours. Upon completion of the reaction, the reaction was quenched with deionized water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 3-(bromomethyl)-2-methoxypyridine (829 mg, 70%) as a colorless oil.
1H NMR (CDCl3) δ: 8.14 (dd, J = 5.0, 1.9 Hz, 1H), 7.63 (dd, J = 7.3, 1.9 Hz, 1H), 6.89 (dd, J = 7.3, 5.0 Hz, 1H), 4.51 (s, 2H), 4.04 (s, 3H).
