2-Trifluoromethylbenzenesulphonyl chloride → ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate

HRID 504733

반응식

HRID 504733 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[F:29][C:17]([F:16])([F:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)(=[O:25])=[O:26]

참가 물질

4

반응물 2

HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

생성물 1

HCID 57476178ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylate수율 88.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of ethyl 7-amino-1H-indole-2-carboxylate (4.1 g) and pyridine (60 mL) was added 2-trifluoromethylbenzenesulfonyl chloride (5.0 g) under ice-cooling, and the mixture was stirred from under ice-cooling to room temperature for 18 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate. The solution was washed with aqueous citric acid solution and saturated brine, and filtrated through silica gel. The eluate was concentrated under reduced pressure, and the obtained pale-brown oil was crystallized from ethyl acetate-hexane to give the title compound (7.3 g, yield 88%) as pale-brown crystals. MS: 413 (MH+). melting point: 138-139° C.

후처리

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. washThe solution was washed with aqueous citric acid solution and saturated brine
  5. filtrationfiltrated through silica gel
  6. concentrationThe eluate was concentrated under reduced pressure
  7. customthe obtained pale-brown oil was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-74adccb462f24218a7d33daf25772b36
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777047B2

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