tert-Butyl {5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbamate → tert-Butyl {5-[(Z)-2-(3-aminophenyl)vinyl]pyridin-3-yl}carbamate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
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.