Dichloromethane → 3-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561667Notes

Reaction equation

HRID 561667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:21]2[CH2:23][CH2:22]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:35])C=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:21]2[CH2:23][CH2:22]2)[C:9]2[C:17]3[C:12](=[C:13]([CH2:18][S:19]([CH3:20])=[O:35])[CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583921383-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922543-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indoleYield 130.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.29 mmol) of the compound from Example 227 were introduced into 15 ml of dichloromethane at 0° C., 72 mg (0.29 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 crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 135 mg of the title compound as mixture of diastereomers.

Workup

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

Sources & evidence

ORD record
ord-32d3d8266a0d4e83aa39823b0ab866ba
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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