tert-Butyl {3-[(3-aminophenyl)ethynyl]phenyl}carbamate → tert-Butyl {3-[2-(3-aminophenyl)ethyl]phenyl}carbamate

Participants

Reaction Steps

To a solution of tert-butyl {3-[(3-aminophenyl)ethynyl]phenyl}carbamate (0.5 g, 2.0 mmol) in methanol (10 mL) was added 10% palladium on carbon (0.50 g, 0.43 mmol) and the mixture was stirred under an atmosphere of hydrogen for 24 h. The reaction mixture was filtered through a pad of celite, rinsed with methanol and dichloromethane. The solvents were evaporated to give a crude oil. This material was purified by flash column chromatography to yield the desired product (430 mg, 85%). LCMS for C19H25N2O2(M+H)+: m/z=313.2.

Provenance & Evidence