Potassium Phosphate, Tribasic → 6-(benzylthio)-1-(2,3'-difluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinolin-2(1H)-one

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Reaction Conditions

Reaction Steps

A vial was charged with 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methoxyphenyl)quinolin-2(1H)-one (0.200 g, 0.425 mmol), (3-fluorophenyl)boronic acid (0.065 g, 0.468 mmol), potassium phosphate, dibasic (0.296 g, 1.701 mmol), and PdCl2(dppf) (0.031 g, 0.043 mmol)). The vial was flushed with Ar (g), then 1,4-dioxane (1.134 ml) and water (0.567 ml) were added. The vial was sealed and heated in a Biotage Initiator microwave reactor for 1 h at 90° C. LCMS showed clean desired product. The mixture was extracted with EtOAc (3×), then the combined organic extracts were concentrated. The residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-50%, then 50-100% EtOAc/Heptane) to give 6-(benzylthio)-1-(2,3′-difluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinolin-2(1H)-one (0.154 g, 0.317 mmol, 74.6% yield). m/z (ESI) 486.0 (M+H)+.

Provenance & Evidence