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

HRID 561705Notes

Reaction equation

HRID 561705 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])O)=[C:16]([F:30])[CH:15]=1.FC1C=CC(C(C2C=CC(F)=CC=2)C2C3C(=C(CSC)C=CC=3)NC=2)=CC=1.FC(F)(F)C(O)=O>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[C:9]2[C:8]3[C:12](=[C:4]([CH2:3][S:2][CH3:1])[CH:5]=[CH:6][CH:7]=3)[NH:11][CH:10]=2)=[C:16]([F:30])[CH:15]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 583921273-[Bis(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 58392225(4-Chloro-2-fluorophenyl)(2,4-difluorophenyl)methanol

Product 1

HCID 583925453-[(4-Chloro-2-fluorophenyl)(2,4-difluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Conditions

Temperature
80 °C

Procedure

The title compound was prepared starting from 750 mg (4.23 mmol) of the compound from Example 8A and 1.15 g (4.23 mmol) of the compound from Example 181A in analogy to the synthesis of the compound from Example 278. A difference was that stirring at 80° C. for two days was followed by addition of 0.33 ml (4.23 mmol) of trifluoroacetic acid and stirring for an additional 16 h. 65 mg (75% purity, 3% of theory) of the target compound were obtained.

Workup

  1. stirringstirring for an additional 16 h
  2. custom65 mg (75% purity, 3% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-5f4298e58ef545c0ad6d0888a78ecbf3
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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