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

HRID 1960357

反応式

HRID 1960357 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-065c0478d1fd41e28838e9bfb4ce1d9c
出典データセット
uspto-grants-2013_04
特許番号
US08410087B2

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