Sodium Carbonate → 2-(4-Fluoro-phenyl)-4-methyl-6-(4-trifluoromethyl-phenyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-chloro-4-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (270 mg, 1.0 mmol), 4-fluorobenzeneboronic acid (155 mg, 1.0 mmol), 2N Na2CO3 (1.5 mL) in DME (10 mL) was added tetrakis(triphenylphosphine)palladium (70 mg, 0.06 mmol) under argon. The mixture was heated to 85° C. for 6 h, cooled to room temperature, diluted with water, and extracted with methylene chloride (3×). The organic solution was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (5-20% methylene chloride in heptane) to give the product as an off white solid (275 mg, 83%). 1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=7.91 Hz, 2H), 8.12 (dd, J=5.27, 9.04 Hz, 2H), 7.74 (d, J=8.29 Hz, 2H), 7.54 (d, J=3.01 Hz, 2H), 7.18 (t, J=8.67 Hz, 2H), 2.50 (s, 3H). MS m/e 332.3 (M+H)

Provenance & Evidence