m-Chloroperbenzoic acid → HCID 117988988, compound
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([S:14][C:15]1[C:16]([C:21]2[N:33]([CH3:34])[C:24]3=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=[C:23]3[N:22]=2)=[N:17][CH:18]=[CH:19][N:20]=1)[CH3:13].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:12]([S:14]([C:15]1[C:16]([C:21]2[N:33]([CH3:34])[C:24]3=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=[C:23]3[N:22]=2)=[N:17][CH:18]=[CH:19][N:20]=1)=[O:6])[CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
467 mg of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 425 mg of 2-(3-ethylsulfanylpyrazin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine and 8 ml of chloroform under ice cooling. The mixture was heated to room temperature and stirred at room temperature for 1 hour. 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 dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 205 mg of 2-(3-ethylsulfinylpyrazin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 7) and 230 mg of 2-(3-ethylsulfonylpyrazin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 8).
Workup
- 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-53750772551c4f2c9656e4de5f1979ea
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09364000B2
Reaction notes
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