In a microwave vial containing ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-2-carboxylate (K4) (0.23 g, 0.69 mmol), 4-(bromomethyl)-2-methoxypyridine (M3) (0.17 g, 0.83 mmol), and palladium tetrakis (0.52 g, 0.45 mmol) was, added 4.0 mL toluene, 2.8 mL, ethanol, and 1.0 mL 2.0 M aqueous Na2CO3. The resulting solution was heated to 85° C. for 30 minutes, filtered through Celite, and washed with excess ethyl acetate. The filtrate was washed twice with water, washed with brine, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-100% ethyl acetate in hexanes to afford ethyl 4-[(2-methoxypyridin-4-yl)methyl]quinoline-2-carboxylate (M4) that gave a mass ion (ES+) of 323.3 for M+H+.
