Water → 3-Amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

HRID 379721

반응식

HRID 379721 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=1.[H-].[Na+].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].O>CN(C=O)C>[NH2:7][C:6]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:9][CH:8]=2)[N:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:19]=1[C:20](=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 183678884-Chloro-2-[(ethoxycarbonyl)amino]benzonitrile

생성물 1

HCID 183678333-Amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-chloro-2-(ethoxycarbonylamino)benzonitrile (10.8 g) in DMF (50 ml) cooled to 0° C. was added sodium hydride (60% w/w dispersion in mineral oil, 2.0 g, 50 mmol). The mixture was stirred for 30 min at 0° C. and then 2-bromoacetophenone (9.9 g, 50 mmol) was carefully added. After stirring for an additional 15 h at 0° C., the mixture was poured into water (500 ml) and extracted with diethyl ether (500 ml×2). After drying (MgSO4) and removal of solvent, the crude product was purified by flash chromatography eluting with ethyl acetate/hexane (1:5) to afford 11.8 g (72%) of the title compound as a brown amorphous solid.

후처리

  1. stirringAfter stirring for an additional 15 h at 0° C.
  2. extractionextracted with diethyl ether (500 ml×2)
  3. customAfter drying
  4. custom(MgSO4) and removal of solvent
  5. customthe crude product was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:5)

출처 및 근거

ORD 기록
ord-12066afaf31c4f06a4ac9a1e53cca32c
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300363B1

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