Ethyl bromoacetate → ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2)([O-:3])=[O:2].[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[CH2:25]([O:24][C:22]([CH2:21][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH:9]=[C:10]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:23])[CH3:26]Participants
Procedure
To a solution of ethyl 7-nitro-1H-indole-2-carboxylate (2.00 g, 8.45 mmol) in N,N-dimethylformamide (50 ml) was added 60% sodium hydride (0.34 g, 8.54 mmol), and the reaction mixture was stirred at room temperature until it became transparent. Then, ethyl bromoacetate (1.43 g, 8.54 mmol) was added and the resulting mixture was stirred at 50-60° C. for 4 hours. The reaction mixture was cooled to room temperature and poured into ice water, followed by extraction with ethyl acetate (three times). The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate (2.11 g).
Workup
- stirringthe resulting mixture was stirred at 50-60° C. for 4 hours
- temperatureThe reaction mixture was cooled to room temperature
- extractionfollowed by extraction with ethyl acetate (three times)
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)
Sources & evidence
- ORD record
- ord-f51fd5c0e69346bbb211aa115eebc3d0
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271251B1
Reaction notes
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