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Dichloromethane → 3-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfinyl)methyl]-1H-indole

HRID 561593
Notes
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Reaction equation

HRID 561593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH:10]2[CH2:12][CH2:11]2)[CH3:9])=[C:4]([F:25])[CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23]([CH3:24])=[O:37])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([CH:10]2[CH2:12][CH2:11]2)[CH3:9])=[C:4]([F:25])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583922333-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583925433-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfinyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

100 mg (0.27 mmol) of the compound from Example 97 were introduced into 18 ml of dichloromethane at 0° C., 66 mg (0.27 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 solvents were removed in vacuo. The residue was taken up in ethyl acetate and washed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 86 mg (83% of theory) of the title compound as mixture of diastereomers.

Workup

  1. customthe solvents were removed in vacuo
  2. washwashed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. customThe solvents were removed in vacuo
  4. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-bf0c8d552e664a1a924c7e2f22430b7a
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes