Trifluoroacetic acid → 3-[(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561673Notes

Reaction equation

HRID 561673 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([CH:11]2[CH2:13][CH2:12]2)O)=[C:4]([F:14])[CH:3]=1.FC(F)(F)C(O)=O.[CH3:22][S:23]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:35]=1[NH:34][CH:33]=[CH:32]2)(=[O:25])=[O:24]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([CH:11]2[CH2:13][CH2:12]2)[C:32]2[C:31]3[C:35](=[C:27]([CH2:26][S:23]([CH3:22])(=[O:25])=[O:24])[CH:28]=[CH:29][CH:30]=3)[NH:34][CH:33]=2)=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58392245(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methanolHCID 583922947-[(Methylsulfonyl)methyl]-1H-indole

Product 1

HCID 583923233-[(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

104 mg (0.48 mmol) of the compound from Example 156A and 0.04 ml (0.57 mmol) of trifluoroacetic acid were added to 100 mg (0.48 mmol) of the compound from Example 86A in 4 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). 100 mg (51% 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-89ee493ec398401695719726575686d3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…