m-Chloroperbenzoic acid → HCID 71246892, compound
Reaction equation
[CH2:1]([S:3][C:4]1[C:5]([C:10]2[N:23]([CH3:24])[C:13]3=[N:14][CH:15]=[C:16]([S:18][C:19]([F:22])([F:21])[F:20])[CH:17]=[C:12]3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([S:3]([C:4]1[C:5]([C:10]2[N:23]([CH3:24])[C:13]3=[N:14][CH:15]=[C:16]([S:18][C:19]([F:22])([F:20])[F:21])[CH:17]=[C:12]3[N:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:33])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (200 mg), m-chloroperbenzoic acid (purity: not less than 65%) (230 mg) and chloroform (10 ml) was stirred while ice-cooling for 5 hours. To the reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfinyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (89 mg), which is hereinafter referred to as “the present compound 14”, and 2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (130 mg), which is hereinafter referred to as “the present compound 15”.
Workup
- temperaturecooling for 5 hours
- extractionthe mixture was extracted with chloroform
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-76440eb84a064ab1bed6bf8883221ed4
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353110B2
Reaction notes
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