HCID 86663049, compound → HCID 86663051, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N+:15]([O-])=O)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1>[Ni].C1COCC1>[NH2:15][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]=[C:2]([Br:1])[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]=3[NH:6][C:7]=2[CH:8]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of methyl 2-bromo-7-nitro-5H-pyrido[3,2-b]indole-4-carboxylate (1.00 g, 2.86 mmol) and Raney nickel (1.0 g, 17 mmol, 2800 nickel slurry in water) was stirred in THF (50 mL) under H2 (balloon) for 1.5 hr. This was filtered and the filter cake was washed with warn THF (100 mL). Removal of the solvent left methyl 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (700 mg, 2.08 mmol, 73% yield) as a solid. MS (ESI) m/z 321.94 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.27 (1H, br. s.), 7.78 (1H, d), 7.62 (1H, s), 6.79 (1H, br. s.), 6.60 (1H, d, J=8.5), 5 84 (2H, br. s.), 4.00 (3H, s).