m-Chloroperbenzoic acid → 5-[[(4-Fluorophenyl)sulfonyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:10]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])[C:11]2[C:12]([CH3:20])=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:10]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=2[F:29])[C:11]2[C:12]([CH3:20])=[CH:13][C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)(=[O:38])=[O:9])=[CH:4][CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 5-[[(4-fluorophenyl)sulfinyl](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (106 mg, 0.25 mmol) in methylene chloride (5 ml), 3-chloroperbenzoic acid (66 mg, 0.25 mmol) was added at 0° C. After stirring for 5 days at room temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to preparative thin-layer chromatography (developed with hexane:ethyl acetate=2:3, eluted with methylene chloride:methanol=4:1). The obtained fraction was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and was collected by filtration, to obtain the title compound (67 mg, 0.15 mmol, 61%) as a white solid.