General procedure for the synthesis of 2-bromo-3-methoxy-6-methylpyridine from 2-bromo-3-hydroxy-6-methylpyridine and iodomethane: 2-bromo-3-hydroxy-6-methylpyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol), and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) were mixed in acetone (100 mL) in acetone was stirred. The reaction mixture was heated to reflux overnight. Upon completion of the reaction, the mixture was filtered, the solvent was evaporated and purified by silica gel column chromatography (eluent: hexane/ethyl acetate, 95:5 to 9:1) to afford the target product 2-bromo-3-methoxy-6-methylpyridine as a white solid (7.49 g, 88.3% yield).1H NMR (500 MHz, CDCl3): δ 2.46 (s, 3H), 3.87 (s, 3H), 3.87 (s, 3H). 3.87 (s, 3H), 7.04 (d, J = 8.0 Hz, 1H), 7.10 (d, J = 8.0 Hz, 1H).
