Sodium Carbonate → 4'-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (400 mg), (4-methoxycarbonylphenyl)boronic acid (275 mg), dichlor(1,1′-bis(diphenyl-phosphino)-ferrocene)palladium (II) dichloromethane adduct (41 mg) in dioxane (3 mL) and water (2.6 mL) was added a 2 M aqueous sodium carbonate solution (1.52 mL). The mixture was stirred at 80° C. for 1.5 h. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield the title compound as a yellow foam (400 mg, 88%), MS (ESI+): m/z=450.2063 ([M+H]+).

Provenance & Evidence