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

HRID 561659Notes

Reaction equation

HRID 561659 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([Cl: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>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([CH:1]2[CH2:3][CH2:2]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)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 866794-Chloro-alpha-cyclopropylbenzenemethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583921383-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

515 mg (2.82 mmol) of the compound from Example 153A and 0.26 ml (3.39 mmol) of trifluoroacetic acid were added to 500 mg (2.82 mmol) of the compound from Example 8A in 20 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 500 mg (50% 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-030c8b85c683487d97e7218ce10012af
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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