Sodium Thiosulfate → 2-(5-ethylsulfonyl-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-6-trifluoromethylthiazolo[5,4-b]pyridine
Reaction equation
Cl[C:2]1C=C(C=C[CH:11]=1)C(OO)=O.C(S[C:15]1[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:16]=1[C:25]1[S:26][C:27]2[C:32]([N:33]=1)=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][N:28]=2)C.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:38]([C:15]1[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[C:16]=1[C:25]1[S:26][C:27]2[C:32]([N:33]=1)=[CH:31][C:30]([C:34]([F:36])([F:37])[F:35])=[CH:29][N:28]=2)(=[O:42])=[O:40])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.31 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.21 g of 2-(5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-6-trifluoromethylthiazolo[5,4-b]pyridine and 4 ml of chloroform, under ice cooling, and the mixture was stirred at room temperature for 6 hours. A 10% aqueous sodium thiosulfate solution was poured into 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 magnesium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.24 g of 2-(5-ethylsulfonyl-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-6-trifluoromethylthiazolo[5,4-b]pyridine (Compound of Present Invention (28)).
Workup
- extractionthe mixture was extracted with chloroform
- washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-250e7a6b3e6248abb0d868497b40906c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120792B2
Reaction notes
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