Dichloromethane → 3-{(4-Fluorophenyl) [4-(trifluoromethyl)phenyl]methyl}-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561594Notes

Reaction equation

HRID 561594 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[C:9]2[C:17]3[C:12](=[C:13]([CH2:18][S:19][CH3:20])[CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:42])C=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=2)[C:9]2[C:17]3[C:12](=[C:13]([CH2:18][S:19]([CH3:20])=[O:42])[CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583923633-{(4-Fluorophenyl)[4-(trifluoromethyl)phenyl]methyl}-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583923923-{(4-Fluorophenyl) [4-(trifluoromethyl)phenyl]methyl}-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

75 mg (0.18 mmol) of the compound from Example 99 were introduced into 25 ml of dichloromethane at 0° C., 43 mg (0.18 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT for 2 h. 2 ml of methanol were added, and the solution was concentrated. The residue was purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient). 65 mg (84% of theory) of the title compound were obtained as mixture of diastereomers.

Workup

  1. concentrationthe solution was concentrated
  2. customThe residue was purified twice by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-3cfa300bbc0a4599b8653bdd45b8d04b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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