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

HRID 345665노트

반응식

HRID 345665 반응식
[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

참가 물질

5

반응물 3

HCID 5798Benzimidazole2회HCID 24758Sodium hydride2회HCID 104695051H-Pyrrole-2,5-dione, 3-bromo-4-(1H-indol-3-yl)-

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-480423e30a614a84b306e5a3d663f330
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057614

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