Ethyl bromoacetate → ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate

HRID 650049ノート

反応式

HRID 650049 の反応式
[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]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 250407Ethyl 7-nitro-1H-indole-2-carboxylate

生成物 1

HCID 21714275ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  1. stirringthe resulting mixture was stirred at 50-60° C. for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate (three times)
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

出典と根拠

ORDレコード
ord-f51fd5c0e69346bbb211aa115eebc3d0
出典データセット
uspto-grants-2001_08
特許番号
US06271251B1

反応ノート

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