Reaction #1005969

ord-17f073b2feae43b1b261f41d1a66eacb

Reaction equation

O=C(OO)c1cccc(Cl)c1
3-chloroperoxybenzoic acid
CCSc1cc(C(F)(F)F)ccc1-c1cn2cc(C(F)(F)F)ccc2n1
2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine
O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulfate
CCS(=O)(=O)c1cc(C(F)(F)F)ccc1-c1cn2cc(C(F)(F)F)ccc2n1
2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionthe mixture was extracted with chloroform
  2. 2
    WashThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. 3
    Dryingdried over anhydrous magnesium sulfate
  4. 4
    Concentrationconcentrated under reduced pressure

Procedure

436 mg of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 236 mg of 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine and 5 ml of chloroform under ice cooling, and the mixture was stirred at room temperature for 4 hours. A 10% 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 magnesium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 122 mg of 2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 7).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09271500B2uspto-grants-2016_03