Sodium Carbonate → [2-(3,5-Bis-trifluoromethyl-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-acetic acid methyl ester

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Reaction Conditions

Reaction Steps

To a degassed solution of [2-chloro-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-acetic acid methyl ester (165 mg, 0.5 mmol), 3,5-di(trifluoromethyl)benzeneboronic acid (160 mg, 0.6 mmol), 2N Na2CO3 (1.0 mL) in DME (9 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 (0-20% ethyl acetate in methylene chloride) to give the product as a white solid (150 mg, 59%). 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 2H), 8.24 (d, J=8.29 Hz, 2H), 7.96 (s, 1H), 7.73-7.85 (m, 4H), 3.83 (s, 2H), 3.78 (s, 3H). MS m/e 508.2 (M+H).

Provenance & Evidence