Dichloromethane → tert-butyl [2-[[3'-ethoxy-4'-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]oxy]ethyl][(2R)-2-hydroxy-2-phenylethyl]carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl [(2R)-2-hydroxy-2-phenylethyl][2-(4-iodophenoxy)ethyl]carbamate (250 mg), [3-ethoxy-4-[[(methylsulfonyl)amino]carbonyl]phenyl]boronic acid (223 mg), [1,1′-bis(diphenylphosphino]ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1, 114 mg), 1,1′-bis(diphenylphosphino)ferrocene (32 mg), N,N-dimethylformamide (5 ml), and 2N sodium carbonate solution (0.99 ml) was stirred at 80° C. for 1 hour. After cooling to room temperature, the mixture was quenched by the addition of 1N hydrochloric acid (1.99 ml) and partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated, washed with water (20 ml×2) and brine (20 ml), and dried over magnesium sulfate. Filtration followed by evaporation gave a brown foam which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give tert-butyl [2-[[3′-ethoxy-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]oxy]ethyl][(2R)-2-hydroxy-2-phenylethyl]carbamate (84.5 mg) as a pale orange solid.

Provenance & Evidence