Methanol → 3-{4-[3-(2-fluoro-5-trifluoromethyl-phenyl)ureido]phenyl}-1-methyl-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[N:12]=[C:13]=[O:14].[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[C:17]1[C:32]([NH2:34])=[O:33].CO>O1CCCC1>[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:14])[NH:31][C:28]1[CH:27]=[CH:26][C:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]([CH3:15])[C:17]=2[C:32]([NH2:34])=[O:33])=[CH:30][CH:29]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.075 g of 2-fluoro-5-trifluoromethylphenyl isocyanate is added to a solution of 0.086 g of 1-methyl-3-(4-aminophenyl)-1H-indole-2-carboxamide in 18 ml of tetrahydrofuran and the stirring is continued for 1 hour. 5 ml of methanol are added, the reaction mixture is then concentrated under reduced pressure, and the residue is purified by chromatography on a silica column, elution being carried out with a mixture of cyclohexane and ethyl acetate (20/80 by volume), to give 90 mg of 3-{4-[3-(2-fluoro-5-trifluoromethyl-phenyl)ureido]phenyl}-1-methyl-1H-indole-2-carboxamide, the characteristics of which are as follows:
Workup
- concentrationthe reaction mixture is then concentrated under reduced pressure
- customthe residue is purified by chromatography on a silica column, elution
- additionbeing carried out with a mixture of cyclohexane and ethyl acetate (20/80 by volume)
Sources & evidence
- ORD record
- ord-0720af291a20462cbc6a8a437418d5b7
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07566736B2
Reaction notes
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