Trifluoroacetic acid → 2-(1-{7-[(Methylsulfanyl)methyl]-1H-indol-3-yl}-1-[4-(trifluoromethyl)phenyl]ethyl)cyclopropanecarbonitrile
Reaction equation
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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux overnight
- concentrationIt was concentrated
- customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
Sources & evidence
- ORD record
- ord-ec71517e0efa4786aa14c2e684011975
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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