m-Chloroperbenzoic acid → HCID 117988598, compound

HRID 2201359Notes

Reaction equation

ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([S:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[N:33]([CH3:34])[C:24]2=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=[C:23]2[N:22]=1)[CH3:13].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([S:14]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[N:33]([CH3:34])[C:24]2=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=[C:23]2[N:22]=1)=[O:6])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

448 mg of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 420 mg of 2-(4-ethylsulfanylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 9 ml of chloroform under ice cooling. The mixture was stirred at 0° C. for 1 hour, then stirred at room temperature for 30 minutes. A saturated aqueous sodium bicarbonate solution was poured to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 215 mg of 2-(4-ethylsulfinylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 10) and 211 mg of 2-(4-ethylsulfonylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 11).

Workup

stirringstirred at room temperature for 30 minutes
extractionthe mixture was extracted with chloroform
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c827d04b303146b3b4970a9e13e0150d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364000B2

Reaction notes

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