Dichloromethane → 3-[Bis(4-chlorophenyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561711Notes

Reaction equation

HRID 561711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[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:39])C=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[C:9]2[C:17]3[C:12](=[C:13]([CH2:18][S:19]([CH3:20])=[O:39])[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 583922363-[Bis(4-chlorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583921253-[Bis(4-chlorophenyl)methyl]-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg (0.49 mmol) of the compound from Example 279 were introduced into 20 ml of dichloromethane at 0° C., 120 mg (0.49 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 134 mg (65% of theory) 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-7a10e230fef34a36b378adff4e34819c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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