Sodium Carbonate → Methyl E-4-{2-[2-(4-cyanophenyl)ethyl]-4-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]but-3-enyl}benzoate

Participants

Reaction Steps

270 mg (0.47 mmol) of methyl E-4-{4-[2-(4-bromobenzyloxy)phenyl]-2-[2-(4-cyanophenyl)ethyl]but-3-enyl}benzoate from Example 18A are dissolved in 3 ml of 1,2-dimethoxyethane and, under argon, 106 mg (0.56 mmol) of 4-trifluoromethylphenylboronic acid, 3.3 mg of bis(triphenylphosphine)palladium(II) chloride and 0.51 ml of a 2 M solution of sodium carbonate in water are added. The reaction mixture is then stirred under reflux for 12 hours. The mixture is subsequently cooled, filtered through 1 g of Extrelut, washed with dichloromethane and concentrated. The resulting crude product is purified by preparative HPLC. 175 mg (0.27 mmol, 58% yield) of a colorless solid are obtained.

Provenance & Evidence