N-[3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide → 2-(4-methoxy-phenyl)-7,7-dimethyl-5-(3-methyl-butyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one
Reaction equation
[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[N:4]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:3]1=[O:30]>[Ni]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[NH:11][C:8]3=[CH:9][C:10]4[C:2]([CH3:1])([CH3:31])[C:3](=[O:30])[N:4]([CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]=4[CH:6]=[C:7]3[N:22]=2)=[CH:14][CH:15]=1Participants
3
Procedure
2-(4-Methoxy-phenyl)-7,7-dimethyl-5-(3-methyl-butyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one is prepared from N-[3,3-dimethyl-1-(3-methyl-butyl)-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-methoxy-benzamide (167 mg) as described in Example 1b using Raney-nickel (25 mg). After aqueous work-up 2-(4-methoxy-phenyl)-7,7-dimethyl-5-(3-methyl-butyl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (120 mg) is obtained by flash chromatography on silica gel eluting with light petroleum/EtOAc (1:1).
Sources & evidence
- ORD record
- ord-1b16c7c63836412cace22fb26d0036b0
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07714010B2
Reaction notes
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