tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate → tert-Butyl {5-[(Z)-2-(3-aminophenyl)vinyl]pyridin-3-yl}carbamate

Participants

Reaction Steps

Into a reaction flask were added tert-butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate (0.45 g, 1.4 mmol) (prepared in Example C19, step A), methanol (15 mL) and 100 mg of Lindlar's catalyst. The reaction mixture was hydrogenated at 35 psi for 2 h. After removal of the solvent, the crude was purified by silica gel column chromatography to give the desired product as a white powder (0.19 g, 42%). LCMS for C18H22N3O2 (M+H)+: m/z=312.0.

Provenance & Evidence