Sodium Carbonate → Methyl 4'-[2-[[(benzyloxy)carbonyl]amino]ethyl]-2-methyl-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-N-[2-(4-bromophenyl)ethyl]-carbamate (1.3 g) in 1,2-dimethoxyethane (20 ml) was added [4-(methoxycarbonyl)-2-methylphenyl]boronic acid (792 mg), tetrakis(triphenylphosphine)palladium (360 mg) and aqueous solution of sodium carbonate (2M, 4.1 ml), and the mixture was stirred at 80° C. for 2 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[[(benzyloxy)carbonyl]amino]ethyl]-2-methyl-1,1′-biphenyl-4-carboxylate (660 mg).

Provenance & Evidence