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Trifluoroacetic acid → 2-[(2-Fluoro-4-methylphenyl){5-fluoro-7-[(methylsulfonyl)methyl]-1H-indol-3-yl}methyl]cyclopropanecarbonitrile

HRID 561694
Notes
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Reaction equation

HRID 561694 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[F:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH:20](O)[CH:21]1[CH2:23][CH:22]1[C:24]#[N:25].[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[C:35]([CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:36]=1)[NH:33][CH:32]=[CH:31]2>ClCCCl>[F:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH:20]([C:31]1[C:30]2[C:34](=[C:35]([CH2:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:36]=[C:28]([F:27])[CH:29]=2)[NH:33][CH:32]=1)[CH:21]1[CH2:23][CH:22]1[C:24]#[N:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583923185-Fluoro-7-[(methylsulfonyl)methyl]-1H-indoleHCID 583923462-[(2-Fluoro-4-methylphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Product 1

HCID 583924642-[(2-Fluoro-4-methylphenyl){5-fluoro-7-[(methylsulfonyl)methyl]-1H-indol-3-yl}methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

347 mg (1.57 mmol) of indium(III) chloride and 0.18 ml (2.35 mmol) of trifluoroacetic acid were added to 268 mg (1.31 mmol) of the compound from Example 166A and 405 mg (1.57 mmol) of the compound from Example 87A with a purity of 88% under argon in 10 ml of 1,2-dichloroethane, and the mixture was heated under reflux overnight. It was concentrated and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 358 mg (66% of theory) of the title compound as mixture of diastereomers.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationIt was concentrated
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. 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-1f1638211ab442369665d02962b9d0c7
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes