Dichloromethane → 3-Methyl-4-{7-[(methylsulfinyl)methyl]-1H-indol-3-yl}-4-[4-(trifluoromethyl)phenyl]butanonitrile

HRID 561574Notes

Reaction equation

HRID 561574 reaction equation
[CH3:1][CH:2]([CH:6]([C:17]1[C:25]2[C:20](=[C:21]([CH2:26][S:27][CH3:28])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH2:3][C:4]#[N:5].ClCCl.ClC1C=CC=C(C(OO)=[O:40])C=1>CO>[CH3:1][CH:2]([CH:6]([C:17]1[C:25]2[C:20](=[C:21]([CH2:26][S:27]([CH3:28])=[O:40])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:15])([F:14])[F:16])=[CH:9][CH:8]=1)[CH2:3][C:4]#[N:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583924793-Methyl-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}-4-[4-(trifluoromethyl)phenyl]butanonitrile

Product 1

HCID 583923243-Methyl-4-{7-[(methylsulfinyl)methyl]-1H-indol-3-yl}-4-[4-(trifluoromethyl)phenyl]butanonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

150 mg (0.37 mmol) of the compound from Example 54 were introduced into 20 ml of dichloromethane at 0° C., 92 mg (0.37 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). 150 mg (96% 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-af1f4658539f4a8fad7a58fe8d6cf730
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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