Trifluoroacetic acid → 3-[(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561676Notes

Reaction equation

HRID 561676 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.[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[NH:28][CH:27]=[CH:26]2>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:26]2[C:25]3[C:29](=[C:30]([CH2:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:31]=[C:23]([F:22])[CH:24]=3)[NH:28][CH:27]=2)=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58392245(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methanolHCID 583923185-Fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Product 1

HCID 583921653-[(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

96 mg (0.44 mmol) of the compound from Example 156A 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 3 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). 162 mg (86% 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-24da6ea17b374dd4bdcfe0906fe97368
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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