Potassium Fluoride → HCID 59820948, compound

Participants

Reaction Steps

A mixture of methyl N-(5-chloro-2,4-dimethoxyphenyl)-N-[4-(tert-butyl)benzyl]oxamate (800 mg, 1.91 mmol), 4-(trifluoromethoxy)benzeneboronic acid (549 mg, 2.67 mmol), palladium(II) acetate (21 mg, 0.095 mmol), potassium fluoride (332 mg, 5.72 mmol), 2-(di-tert-butylphosphino)biphenyl (57 mg, 0.191 mmol) and tetrahydrofuran (3.0 ml) was refluxed for 5 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (140 mg, 14%) as a pale yellow oil.

Provenance & Evidence