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

HRID 561627노트

반응식

HRID 561627 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ec71517e0efa4786aa14c2e684011975
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

반응 노트

불러오는 중…