Sodium hydride → 3-[1-[3-(2-imidazolylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione
Reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[C:20](=[O:42])[NH:21][C:22](=[O:41])[C:23]=2[C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][CH2:34][CH2:35]OS(C)(=O)=O)[CH:25]=2)=[CH:11]1>CN(C=O)C>[NH:5]1[CH:6]=[CH:7][N:8]=[C:4]1[S:3][CH2:35][CH2:34][CH2:33][N:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([C:23]2[C:22](=[O:41])[NH:21][C:20](=[O:42])[C:19]=2[C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]([CH3:9])[CH:11]=2)=[CH:25]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
7 mg of a 80% dispersion of sodium hydride in mineral oil was added to a cooled solution of 23 mg of 2-mercaptoimidazole in 10 ml of DMF. The mixture was stirred for 0.5 hour while cooling. 100 mg of the product of Example 58 were added and the mixture was stirred for 2 hours while cooling. The mixture was then allowed to warm to room temperature and was stirred overnight. The solvents were removed under reduced pressure and the residue was chromatographed on silica gel with 10% methanol in dichloromethane to give 20 mg of 3-[1-[3-(2-imidazolylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 130°-132° C.
Workup
- temperaturewhile cooling
- stirringthe mixture was stirred for 2 hours
- temperaturewhile cooling
- stirringwas stirred overnight
- customThe solvents were removed under reduced pressure
- customthe residue was chromatographed on silica gel with 10% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-05321765110e44a9872c36ac99455001
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05057614
Reaction notes
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