Dichloromethane → 3-(5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-yl)-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561646Notes

Reaction equation

HRID 561646 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:14]1[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=1)([CH3:13])[CH2:5][CH2:6][O:7]2.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([C:14]1[C:22]3[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:37])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=1)([CH3:13])[CH2:5][CH2:6][O:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583920983-(5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-yl)-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922953-(5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-yl)-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

75 mg (0.21 mmol) of the compound from Example 193 were introduced into 10 ml of dichloromethane at 0° C., 51 mg (0.21 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).

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-61217ecb0d4746779decc2c762a17ddb
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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