Sodium Thiosulfate → 2-(5-ethylsulfonyl-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 2272909Notes

Reaction equation

HRID 2272909 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[N:37]([CH3:38])[C:28]2=[N:29][CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=[C:27]2[N:26]=1)C.[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([S:39]([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[N:37]([CH3:38])[C:28]2=[N:29][CH:30]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:32]=[C:27]2[N:26]=1)(=[O:43])=[O:41])[CH3:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 1179742552-(5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1179743362-(5-ethylsulfonyl-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.35 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.24 g of 2-(5-ethylthio-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 5 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)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (26)).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c5594c9313b4150aef5f1f1c12e12ac
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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