[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19][CH3:20])[CH:14]=2)[C:3]=1[CH3:21].[OH2:22].C1C[O:26]CC1>[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:20])(=[O:26])=[O:22])[CH:14]=2)[C:3]=1[CH3:21]To a stirring solution of 4-chloro-7-fluoro-3-methyl-2-(3-(methylthio)phenyl)-quinoline (130 mg, 0.41 mmol) (described herein) in THF (5.0 mL) and water (1.0 mL) were sequentially added 4-methylmorpholine n-oxide (144 mg, 1.2 mmol) and osmium tetroxide (1.1 μL, 0.020 mmol). The reaction was stirred at rt for 6 h, then an additional 0.05 eq. osmium tetroxide was added and the reaction stirred for 18 more h. The reaction was then quenched with 10% aqueous sodium thiosulfate solution, concentrated, and partitioned between EtOAc and 10% aqueous sodium thiosulfate solution. The organic layer was washed with brine, dried (MgSO4), and concentrated, affording 4-chloro-7-fluoro-3-methyl-2-(3-(methylsulfonyl)phenyl)quinoline. Mass Spectrum (ESI) m/e=350 (M+1).
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