1,2-Dimethoxyethane → 4-(5-Chloro-2-fluoropyridin-4-yl)-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-fluoro-4-iodopyridine, (257 mg, 1 mmol), 4-carboxymethylphenyl boronic acid (0.2 g, 1.1 mmol) were dissolved in dimethoxyethane in a screw cap test tube and 1.5 mL 2M Na2CO3 was added followed by tetrakis(triphenylphosphine)palladium (50 mg, 0.044 mmol). Argon was bubbled through the reaction mixture for 5 min, the tube was sealed, and then the reaction mixture was heated to 85° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil, which was purified by chromatography on silica (EtOAc 0 to 15% in hexanes) to give 90 mg (0.34 mmol, 34% yield) of 4-(5-chloro-2-fluoropyridin-4-yl)-benzoic acid methyl ester. 1H NMR 500 MHz (CDCl3): 8.24 (s, 1H), 8.10 (d, 2H), 7.48 (d, 2H), 6.89 (d, 1H), 3.91 (s, 3H). LCMS: ES+=257.9.

Provenance & Evidence