Sodium Thiosulfate → 2-(2-methylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine
Reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[N:4]=[C:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1SC.Cl[C:24]1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+].[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:24][S:39]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:3]1[N:2]([CH3:1])[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=[C:5]2[N:4]=1)(=[O:43])=[O:41]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.30 g) and chloroform (9 ml), 69% of 3-chloroperbenzoic acid (0.70 g) was added under ice-cooling, and then heated to room temperature, and stirred for 2 hours. Then, into the mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform 2 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.32 g of 2-(2-methylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 3).
Workup
- additionwas added under ice-
- temperaturecooling
- extractionextracted with chloroform 2 times
- dry with materialThe combined organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ac10290d10b54b66bfc01c7e644d4eb4
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853238B2
Reaction notes
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