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Trifluoroacetic acid → 3-[Cyclopropyl(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561658
Notes
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Reaction equation

HRID 561658 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:20][S:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:31]=1[NH:30][CH:29]=[CH:28]2>ClCCl>[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[C:28]2[C:27]3[C:31](=[C:23]([CH2:22][S:21][CH3:20])[CH:24]=[CH:25][CH:26]=3)[NH:30][CH:29]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 102498alpha-Cyclopropyl-4-fluorobenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922653-[Cyclopropyl(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

188 mg (1.13 mmol) of cyclopropyl(4-fluorophenyl)methanol and 0.10 ml (1.35 mmol) of trifluoroacetic acid were added to 200 mg (1.13 mmol) of the compound from Example 8A in 13 ml of dichloromethane. The reaction mixture was stirred at RT for 15 min, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 267 mg (73% of theory) of the title compound were obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-488d2939469c4be4bcc9f1626474fc05
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