HCID 11720271, compound → 7-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-indole-2-carboxamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:36])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[C:25]([N+:30]([O-])=O)[CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]=2[C:33]([NH2:35])=[O:34])=[CH:17][CH:16]=1>CO.[Pd]>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[NH:23][C:22]([C:33]([NH2:35])=[O:34])=[C:21]2[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:13]([NH:12][C:3]2[CH:4]=[C:5]([C:8]([F:11])([F:9])[F:10])[CH:6]=[CH:7][C:2]=2[F:1])=[O:36])=[CH:20][CH:19]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
3.28 g of palladium-on-charcoal are added to a suspension of 3.42 g (6.82 mmol) of 3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-7-nitro-1H-indole-2-carboxamide in 480 ml of methanol. The reaction mixture is hydrogenated at 30° C. under 3 bar for 2 h in an autoclave, and is then filtered over yridi. The filtrate is evaporated to dryness under reduced pressure. The residue obtained is triturated with ethyl acetate and a small amount of methylene chloride and then filtered. 1.30 g of 7-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-indole-2-carboxamide are obtained in the form of a gray solid.