Dichloromethane → 3-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561589Notes

Reaction equation

HRID 561589 reaction equation
[CH:1]1([C:4]2([C:14]3[C:22]4[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[CH:1]1([C:4]2([C:14]3[C:22]4[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:37])[CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583923643-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583923683-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

62.0 mg (0.18 mmol) of the compound from Example 93 were introduced into 10 ml of dichloromethane at 0° C., 43.5 mg (0.18 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. 2 ml of methanol were added, and the residue after concentration was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 48 mg (74% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationthe residue after concentration
  2. customwas purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-aae4da9dceda4e53ae237db584c11f0b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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