Trifluoroacetic acid → 2-(1-{7-[(Methylsulfanyl)methyl]-1H-indol-3-yl}-1-[4-(trifluoromethyl)phenyl]ethyl)cyclopropanecarbonitrile

HRID 561627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561627
FC(F)(F)C(O)=O.[Cl-].[In+3].[Cl-].[Cl-].O[C:13]([CH:25]1[CH2:27][CH:26]1[C:28]#[N:29])([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH3:14].[CH3:30][S:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:41]=1[NH:40][CH:39]=[CH:38]2>ClCCl>[CH3:30][S:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:41]=1[NH:40][CH:39]=[C:38]2[C:13]([CH:25]1[CH2:27][CH:26]1[C:28]#[N:29])([C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=1)[CH3:14]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583925112-{1-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethyl}cyclopropanecarbonitrile

Produkt 1

HCID 583921542-(1-{7-[(Methylsulfanyl)methyl]-1H-indol-3-yl}-1-[4-(trifluoromethyl)phenyl]ethyl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.02 ml (0.24 mmol) of trifluoroacetic acid and 43.3 mg (0.20 mmol) of indium(III) chloride were added to 50.0 mg (0.20 mmol) of the compound from Example 132A and 69.5 mg (0.39 mmol) of the compound from Example 8A in 2 ml of dichloromethane at RT, and the mixture was heated under reflux overnight. It was concentrated and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 9.0 mg (11% of theory) of the title compound as mixture of diastereomers.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationIt was concentrated
  4. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-ec71517e0efa4786aa14c2e684011975
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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