m-Chloroperbenzoic acid → (1-(5-(4-Methylpyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34]([N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)=[O:35])[CH:32]=4)[C:27]([S:41][CH3:42])=[CH:26]3)=[N:23][CH:24]=2)[CH:14]=1>ClCCl>[CH3:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[CH:24]=[N:23][C:22]([N:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34]([N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)=[O:35])[CH:32]=4)[C:27]([S:41]([CH3:42])=[O:6])=[CH:26]3)=[N:21][CH:20]=2)[CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Chloroperoxybenzoic acid (77%, 0.14 g, 0.62 mmol) in dichloromethane (10 mL) was added at 0° C. to a solution of 269c) (0.33 g, 0.77 mmol) in dichloromethane (40 mL) and the reaction mixture was stirred at room temperature for 3 h. The mixture was then washed successively with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (1×30 mL), dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography [silica gel; dichloromethane with 2% methanol]. White solid. Yield: 0.215 g (63% of theory)
Workup
- washThe mixture was then washed successively with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (1×30 mL)
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was purified by flash column chromatography [silica gel; dichloromethane with 2% methanol]
Sources & evidence
- ORD record
- ord-3f5a21f4fdec488387455d7328602f9f
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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