Sodium Thiosulfate → 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine
Reaction equation
C(S[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:23]([CH3:24])[C:14]2=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]2[N:12]=1)CC.Cl[C:26]1C=CC=C(C(OO)=O)[CH:27]=1.C(=O)([O-])O.[Na+].[S:41]([O-:45])([O-])(=[O:43])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:26]([S:41]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:23]([CH3:24])[C:14]2=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=[C:13]2[N:12]=1)(=[O:45])=[O:43])[CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-(2-propylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.22 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.33 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1.5 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced, pressure. The resulting residue was subjected to silica gel column chromatography to give 0.24 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 9).
Workup
- additionwas added under ice-
- temperaturecooling
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced, pressure
Sources & evidence
- ORD record
- ord-da3afb23cd0a4acb9f0648b99c8fb2b7
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278983B2
Reaction notes
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