Dichloromethane → 3-[(2,4-Difluorophenyl)(4-fluorophenyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561598Notes

Reaction equation

HRID 561598 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C:10]1[C:18]2[C:13](=[C:14]([CH2:19][S:20][CH3:21])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:40])C=1>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[C:10]1[C:18]2[C:13](=[C:14]([CH2:19][S:20]([CH3:21])=[O:40])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583921953-[(2,4-Difluorophenyl)(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583924233-[(2,4-Difluorophenyl)(4-fluorophenyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

75 mg (0.19 mmol) of the compound from Example 103 were introduced into 14 ml of dichloromethane at 0° C., 47 mg (0.19 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 by preparative HPLC (mobile phase: acetonitrile/water gradient). 74 mg (95% of theory) of the title compound were obtained as mixture of diastereomers.

Workup

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

Sources & evidence

ORD record
ord-d418a3f9c5e8445e872ed6ce4a313b73
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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