Sodium Thiosulfate → 6-(2-ethylsulfonylphenyl)-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine
Reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)[CH:3]=1.C(S[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[C:23]2[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:27]([CH3:34])[C:24]2=[N:25][CH:26]=1)C.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:35]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:22]=[C:23]2[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:27]([CH3:34])[C:24]2=[N:25][CH:26]=1)(=[O:39])=[O:37])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.70 g of 3-chloroperbenzoic acid (purity of 65% or more) was added to a mixture of 0.35 g of 6-(2-ethylsulfanylphenyl)-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 10 ml of chloroform under ice cooling, and then the mixture was stirred at room temperature for 4 hours. A 10% aqueous sodium thiosulfate solution and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate and then dried with anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.31 g of 6-(2-ethylsulfonylphenyl)-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention 25).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialdried with anhydrous sodium sulfate
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-417b285ceeba4333b73a1b975040d8ab
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260436B2
Reaction notes
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