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

HRID 561578

Reaction equation

HRID 561578 reaction equation
[CH:1]1([C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)(O)[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2>ClCCl>[CH:1]1([C:4]([C:29]2[C:28]3[C:32](=[C:24]([CH2:23][S:22][CH3:21])[CH:25]=[CH:26][CH:27]=3)[NH:31][CH:30]=2)([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanolHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583921063-[1-Cyclopropyl-1-(4-fluorophenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

559 mg (3.10 mmol) of the compound from Example 77A 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 12 ml of dichloromethane. The reaction mixture was stirred at RT for 30 min and then diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 361 mg (38% of theory) of the title compound.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-0be2306708914b3e9eb50432c2e77ae8
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Linked notes

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