2-Amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile → 2-Amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile
Reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=2)[C:3]=1[C:4]#[N:5]>[Pd].C(OCC)(=O)C>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[CH:7]=[C:6]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=2)[C:3]=1[C:4]#[N:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2-amino-6-(2-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile (3.2 g, 7.2 mmol), 10% Pd—C (0.25 g) and ethyl acetate (1 L) was stirred at room temperature for 12 hrs. under a hydrogen atmosphere (2.5 atm). The reaction mixture was filtered on Celite Pad and the filtration was concentrated under reduced pressure to give starting compound 2, which was used for the next step without further purification (2.6 g, yield 87%).