C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.C(OCC)(=O)C>CCOCC>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH:14]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:15]2[CH:16]=[CH:17][N+:18]([O-:37])=[CH:19][CH:20]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1To a methylene chloride solution (20 ml) of the 4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridine (221 mg, 0.58 mmol) obtained in Example 142 was added 3-chloroperbenzoic acid (100 mg, 0.58 mmol) and the mixture was stirred for 20 hours. The reaction mixture was diluted with ether (60 ml), followed by washing with a saturated aqueous solution of sodium bicarbonate, water and brine. The solution was dried and then filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography (ethyl acetate) to yield the title compound (183 mg, 80%). The compound was then crystallized from ethanol and obtained as colorless needle crystals.
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