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

HRID 504733

Reaktionsgleichung

Reaktionsgleichung von HRID 504733
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 57476178ethyl 7-({[2-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-indole-2-carboxylateAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-74adccb462f24218a7d33daf25772b36
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777047B2

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