Potassium Carbonate → HCID 117737093, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-methylquinolin-4(1H)-one (1.0 g, 2.06 mmol) and 3-fluorophenylboronic acid (0.462 g, 3.30 mmol) in 1,4-dioxane (7.74 mL) and water (2.58 mL) was added potassium carbonate (0.856 g, 6.19 mmol) and tetrakis(triphenylphosphine)palladium (0.239 g, 0.206 mmol). The reaction was sparged with argon and then stirred at 80° C. After 1 hour, the reaction mixture was partitioned between water and ethyl acetate, and the organic layer was concentrated. The crude product was purified by column chromatography, eluting with 10-50% (3:1 ethyl acetate/ethanol) in heptane to provide 6-(benzylthio)-1-(2,3′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-2-methylquinolin-4(1H)-one (1.0 g, 2.0 mmol, 97% yield) as a yellow oil. m/z (ESI) 500.0 (M+H)+.

Provenance & Evidence