Sodium Thiosulfate → 2-(2-ethylsulfonyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine
Reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[CH:20]=[C:19]([S:21][C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:17][C:16]=1[C:26]1[N:41]([CH3:42])[C:29]2=[N:30][CH:31]=[C:32]([C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])[CH:33]=[C:28]2[N:27]=1)C.C(=O)(O)[O-].[Na+].[S:48]([O-:52])([O-])(=[O:50])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:48]([C:15]1[CH:20]=[C:19]([S:21][C:22]([F:23])([F:25])[F:24])[CH:18]=[CH:17][C:16]=1[C:26]1[N:41]([CH3:42])[C:29]2=[N:30][CH:31]=[C:32]([C:34]([F:40])([F:39])[C:35]([F:36])([F:37])[F:38])[CH:33]=[C:28]2[N:27]=1)(=[O:52])=[O:50])[CH3:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.19 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.19 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine and 3 ml of chloroform under ice cooling, and then the mixture was stirred under ice cooling for 2 hours. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.22 g of 2-(2-ethylsulfonyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 10).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e34b96037c8f42c0a8246e4a54ac848a
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156838B2
Reaction notes
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