Dichloromethane → 3-[1-(4-Chloro-2-fluorophenyl)-1-cyclopropylethyl]-7-[(methylsulfinyl)methyl]-1H-indole
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customthe solvents were removed in vacuo
- washwashed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
- customThe solvents were removed in vacuo
- 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
- Patent number
- US08063234B2
Reaction notes
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