Sodium Carbonate → HCID 69102258, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl [3-(4-bromophenyl)propyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (312 mg), [3-isobutoxy-4-(methoxycarbonyl)phenyl]boronic acid (207 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (58.4 mg) and 1,1′-bis(diphenylphosphino)ferrocene (7.93 mg) in N,N-dimethylformamide (3.12 ml) was added 2.0M aqueous sodium carbonate solution (1.25 ml) and the mixture was stirred at 90° C. for 2.5 hours. After cooling to room temperature, palladium was removed by filtration through a Celite cake. The mixture was extracted with ethyl acetate and the extract was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1) to give methyl 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-propyl]-3-isobutoxy-4-biphenylcarboxylate (374 mg) as a yellow solid (foam).

Provenance & Evidence