Trifluoroacetic acid → 3-[Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561677Notes

Reaction equation

HRID 561677 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:16]=[CH:15][C:9]3[O:10][C:11]([F:14])([F:13])[O:12][C:8]=3[CH:7]=2)O)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[F:24][C:25]1[CH:26]=[C:27]2[C:31](=[C:32]([CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=1)[NH:30][CH:29]=[CH:28]2>ClCCl>[CH:1]1([CH:4]([C:6]2[CH:16]=[CH:15][C:9]3[O:10][C:11]([F:14])([F:13])[O:12][C:8]=3[CH:7]=2)[C:28]2[C:27]3[C:31](=[C:32]([CH2:34][S:35]([CH3:38])(=[O:36])=[O:37])[CH:33]=[C:25]([F:24])[CH:26]=3)[NH:30][CH:29]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58392116Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methanolHCID 583923185-Fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Product 1

HCID 445952383-[Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.44 mmol) of the compound from Example 157A and 0.04 ml (0.53 mmol) of trifluoroacetic acid were added to 100 mg (0.44 mmol) of the compound from Example 87A in 5 ml of dichloromethane. The reaction mixture was stirred at RT for 45 min, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 151 mg (78% 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-0bbde19fc05242369e05029fe0bb3454
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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