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

HRID 561536Notes

Reaction equation

HRID 561536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[C:20]3[C:15](=[C:16]([CH2:22][S:23][CH3:24])[CH:17]=[C:18]([F:21])[CH:19]=3)[NH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:12]2[C:20]3[C:15](=[C:16]([CH2:22][S:23]([CH3:24])=[O:33])[CH:17]=[C:18]([F:21])[CH:19]=3)[NH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 583922083-(4-Chlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Product 1

HCID 583922373-(4-Chlorophenyl)-3-{5-fluoro-7-[(methylsulfinyl)methyl]-1H-indol-3-yl}propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

75.0 mg (0.21 mmol) of the compound from Example 9 were introduced into 12 ml of dichloromethane at 0° C., 50.8 mg (0.21 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 25 mg (30% of theory) of the title compound which are contaminated with meta-chlorobenzoic acid. It was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated to result in 23 mg (29% of theory) of the title compound as mixture of diastereomers.

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-26407ff1d7044d3ba9d1dbd895b16457
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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