Benzimidazole → 3-(1-benzimidazolyl)-4-(3-indolyl)-1H-pyrrole-2,5-dione

HRID 345665ノート

反応式

HRID 345665 の反応式
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.Br[C:13]1[C:14](=[O:28])[NH:15][C:16](=[O:27])[C:17]=1[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1>CN(C=O)C>[N:3]1([C:13]2[C:14](=[O:28])[NH:15][C:16](=[O:27])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1

参加物

5

反応物 3

HCID 5798Benzimidazole2 回HCID 24758Sodium hydride2 回HCID 104695051H-Pyrrole-2,5-dione, 3-bromo-4-(1H-indol-3-yl)-

生成物 1

HCID 99019583-(1-benzimidazolyl)-4-(3-indolyl)-1H-pyrrole-2,5-dione収率 3.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

260 mg of a 60% dispersion of sodium hydride in mineral oil were added to a solution of 295 mg of benzimidazole in 10 ml of DMF and the mixture was stirred under nitrogen for 0.5 hour. 582 mg of 3-bromo-4-(3-indolyl)-1H-pyrrole-2,5-dione were added and the mixture was heated to 50° C. for 18 hours. A solution of 767 mg of benzimidazole and 260 mg of sodium hydride in 10 ml of DMF was added and the mixture was heated to 90° C. for 18 hours under nitrogen. The solvent was evaporated and the residue was partitioned between dichloromethane and 2M hydrochloric acid. The precipitate was purified on silica gel with ethyl acetate/petroleum ether. Recrystallization from ethyl acetate gave 25 mg of 3-(1-benzimidazolyl)-4-(3-indolyl)-1H-pyrrole-2,5-dione, m.p. 310°-320° C.

後処理

  1. temperaturethe mixture was heated to 90° C. for 18 hours under nitrogen
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between dichloromethane and 2M hydrochloric acid
  4. customThe precipitate was purified on silica gel with ethyl acetate/petroleum ether
  5. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-480423e30a614a84b306e5a3d663f330
出典データセット
uspto-grants-1991_10
特許番号
US05057614

反応ノート

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