m-Chloroperbenzoic acid → (1-(5-(4-Methoxypyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[CH:21]=[N:22][C:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([C:35]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[O:36])[CH:33]=4)[C:28]([S:43][CH3:44])=[CH:27]3)=[N:24][CH:25]=2)[CH:15]=1>ClCCl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[CH:21]=[N:22][C:23]([N:26]3[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([C:35]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[O:36])[CH:33]=4)[C:28]([S:43]([CH3:44])=[O:6])=[CH:27]3)=[N:24][CH:25]=2)[CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Chloroperoxybenzoic acid (65%; 91.6 mg, 0.345 mmol, 0.8 eq,) was added at 0° C. to a stirred solution of the product 141b) (200 mg, 0.432 mmol, 1.0 eq) in dichloromethane (10 mL). Stirring was continued at this temperature for 30 min and the reaction mixture was then diluted with dichloromethane (10 mL), washed with saturated natrium hydrogen carbonate solution and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography [100-200 mesh silica gel; methanol/ethyl acetate=1:9]. White solid. Yield 70 mg (34% of theory). Melting range: 216-220° C. HPLC (method 6): Rt=7.24 min. Mass spectroscopy: m/z: [M+H]+=478.2.
Workup
- washwashed with saturated natrium hydrogen carbonate solution and brine
- dry with materialdried over sodium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography [100-200 mesh silica gel; methanol/ethyl acetate=1:9]
Sources & evidence
- ORD record
- ord-6a0d813c1576465b9548ad2e4422a248
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
Loading…