Sodium Carbonate → 4'-(1-Benzenesulfonyl-2-oxo-3-phenyl-imidazolidin-4-yl)-biphenyl-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one (100 mg) and 4-carboxyphenylboronic acid (57 mg) in dioxane (0.6 mL) and water (0.4 mL) under argon were added a 2 M aqueous sodium carbonate solution (0.33 mL) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (9 mg). The mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the mixture was filtered. The filtrate was diluted with ethyl acetate and washed with 10% aqueous KHSO4 solution. The org. phase was dried (MgSO4), filtered and concentrated. The product was purified using column chromatography (SiO2, dichloromethane/methanol 1:0=>4:1) to give 4′-(1-benzenesulfonyl-2-oxo-3-phenyl-imidazolidin-4-yl)-biphenyl-4-carboxylic acid (36 mg) as an off-white solid. MS: 497.1 ([M−H]−)

Provenance & Evidence