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

HRID 561662Notes

Reaction equation

HRID 561662 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][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]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:30]2[C:29]3[C:33](=[C:25]([CH2:24][S:23][CH3:22])[CH:26]=[CH:27][CH:28]=3)[NH:32][CH:31]=2)=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392245(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methanol

Product 1

HCID 583922883-[(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

617 mg (2.82 mmol) of the compound from Example 156A 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 overnight, the solvent was removed in vacuo, and the crude product was then purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 155 mg (14% 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-f33acc5dbe9a46fd8466c1820951842d
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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