Sodium Thiosulfate → 2-(4-Ethylsulfonylpyridin-3-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine
Reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][C:26]([C:30]([F:33])([F:32])[F:31])=[CH:25][N:24]=2)C.[S:34]([O-:38])([O-])(=[O:36])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:34]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][C:26]([C:30]([F:32])([F:33])[F:31])=[CH:25][N:24]=2)(=[O:38])=[O:36])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
217 mg of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 146 mg of 2-(4-ethylsulfanylpyridin-3-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine and 5 ml of chloroform under ice cooling, then the mixture was stirred at room temperature for 8 hours. An aqueous sodium thiosulfate solution was poured to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 81 mg of 2-(4-ethylsulfonylpyridin-3-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter, referred to as Compound of Present Invention 43) and 29 mg of 2-(4-ethylsulfonyl-1-oxypyridin-3-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter, referred to as Compound of Present Invention 44).
Workup
- extractionthe mixture was extracted with chloroform
- washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-277e7a86f50c4253870f888c2c9c6a7c
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09364000B2
Reaction notes
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