5-[4-(4-Methoxy-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester → 2-Amino-5-[4-(4-methoxy-phenyl)-imidazol-1-yl]-4-trifluoromethyl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:12]=[CH:11]2)[C:7]([C:23]([F:26])([F:25])[F:24])=[CH:6][C:5]=1[N+:27]([O-])=O>O1CCCC1.[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[N:12]=[CH:11]2)[C:7]([C:23]([F:26])([F:24])[F:25])=[CH:6][C:5]=1[NH2:27]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1.470 g of 5-[4-(4-methoxy-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester in 25 ml of tetrahydrofuran are hydrogenated in presence of 200 mg of palladium on carbon. After filtration of the catalyst the solution is evaporated to dryness and the residue purified by flash chromatography on silica (40-63 μm particle size) with dichloromethane/methanol 98:2, yielding 1.270 g of 2-amino-5-[4-(4-methoxy-phenyl)-imidazol-1-yl]-4-trifluoromethyl-benzoic acid methyl ester as a beige solid. 1H-NMR (DMSO-d6, 400 MHz): 3.80 s, 3H; 3.95 s, 3H; 6.95 d, J=10.4 Hz, 2H; 7.30 s, 2H; 7.40 s, 1H; 7.70 s, 1H; 7.75 s, 1H; 7.78 d, J=10.4 Hz, 2H; 7.80 s, 1H.
Workup
- filtrationAfter filtration of the catalyst the solution
- customis evaporated to dryness
- customthe residue purified by flash chromatography on silica (40-63 μm particle size) with dichloromethane/methanol 98:2
Sources & evidence
- ORD record
- ord-8941b6c76d6a4de2b0e03d83074102dc
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299085B2
Reaction notes
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