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

HRID 561683
Notes
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Reaction equation

HRID 561683 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[CH3:12][S:13]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[NH:24][CH:23]=[CH:22]2)(=[O:15])=[O:14].O[CH:27]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[CH:28]1[CH2:30][CH:29]1[C:31]#[N:32]>ClCCl>[CH3:39][C:36]1[CH:37]=[CH:38][C:33]([CH:27]([C:22]2[C:21]3[C:25](=[C:17]([CH2:16][S:13]([CH3:12])(=[O:15])=[O:14])[CH:18]=[CH:19][CH:20]=3)[NH:24][CH:23]=2)[CH:28]2[CH2:30][CH:29]2[C:31]#[N:32])=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922947-[(Methylsulfonyl)methyl]-1H-indoleHCID 583923442-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

Product 1

HCID 583923492-[(4-Methylphenyl){7-[(methylsulfonyl)methyl]-1H-indol-3-yl}methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

195 mg (0.88 mmol) of indium(III) chloride and 0.11 ml (1.44 mmol) of trifluoroacetic acid were added to 168 mg (0.80 mmol) of the compound from Example 86A and 150 mg (0.80 mmol) of the compound from Example 158A under argon in 9 ml of dichloromethane, and the mixture was heated under reflux for 1 h. It was diluted with dichloromethane and washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium 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 100 mg (33% of theory) of the title compound as mixture of diastereomers.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 h
  3. washwashed with water and saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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-d83169ba98bf44bd8bd7efec78c4fb48
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