m-Chloroperbenzoic acid → 3-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfinyl)methyl]-1H-indol-3-yl}propan-1-ol

HRID 561535Notes

Reaction equation

HRID 561535 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:13]1[C:21]2[C:16](=[C:17]([CH2:23][S:24][CH3:25])[CH:18]=[C:19]([F:22])[CH:20]=2)[NH:15][CH:14]=1)[CH2:10][CH2:11][OH:12].ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:13]1[C:21]2[C:16](=[C:17]([CH2:23][S:24]([CH3:25])=[O:34])[CH:18]=[C:19]([F:22])[CH:20]=2)[NH:15][CH:14]=1)[CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Product 1

HCID 583923453-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfinyl)methyl]-1H-indol-3-yl}propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.25 mmol) of the compound from Example 8 were introduced into 15 ml of dichloromethane at 0° C., 61.9 mg (0.25 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. It was concentrated, and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 91 mg (88% of theory) of the title compound as mixture of diasteromers.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-d952975fab83414eb287692c616dc693
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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