Potassium Carbonate → 5-Methyl-2-phenylpyridine

Participants

Reaction Steps

Phenylboronic acid (732 mg, 6 mmol), 2-bromo-5-methylpyridine (1.03g, 5.99 mmol), and Pd (PPh3)4 (350 mg, 0.303 mmol) were heated in 0.4 M K2CO3 (30 mL, 12 mmol) and CH3CN (30 mL) at 90° overnight. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and ethyl acetate. The organic layer was separated, dried (Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (9:1 hexanes:ethyl acetate) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (m, 1H), 8.05 (m, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.68–7.71 (m, 1H), 7.37–7.50 (m, 3 H), 2.34 (s, 3H); MS (APCI+) m/z 170 (M+H)+.

Provenance & Evidence