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

HRID 533596Notes

Reaction equation

HRID 533596 reaction equation
C(S[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=[C:12]2[N:11]=1)C.Cl[C:25]1C=CC=C(C(OO)=O)[CH:26]=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:25]([S:35]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:17]=[C:12]2[N:11]=1)(=[O:39])=[O:37])[CH3:26]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 867081912-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867081932-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.25 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.43 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1 hour. To the reaction mixture, chloroform was added under ice-cooling, and then saturated aqueous sodium thiosulfate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, then saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystal was washed with hexane, then methyl-tert-butyl ether to give 0.27 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 6).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialsaturated brine, dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained crystal was washed with hexane

Sources & evidence

ORD record
ord-6a957dcf71324c07bb3eaac6223723b5
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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