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Trifluoroacetic acid → 2-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

HRID 561629
Notes
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Reaction equation

HRID 561629 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])(O)[CH3:20])=[CH:15][CH:14]=1.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=1)[NH:33][CH:32]=[CH:31]2>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:22]2[CH2:24][CH:23]2[C:25]#[N:26])([C:31]2[C:30]3[C:34](=[C:35]([CH2:37][S:38][CH3:39])[CH:36]=[C:28]([F:27])[CH:29]=3)[NH:33][CH:32]=2)[CH3:20])=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583923532-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

Product 1

HCID 583923982-[1-(4-Chlorophenyl)-1-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

367 mg (1.66 mmol) of indium(III) chloride and 0.12 ml (1.58 mmol) of trifluoroacetic acid were added to 350 mg (1.58 mmol) of the compound from Example 75A and 308 mg (1.58 mmol) of the compound from Example 11A in 9 ml of dichloromethane at RT, and the mixture was heated under reflux for 15 min. It was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride 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 32.5 mg (5% of theory) of the title compound as mixture of diastereomers.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 min
  3. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride 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-891e9740aaff47efafd63ad8357f1b45
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