Water → 4-Chloro-7-fluoro-3-methyl-2-(3-(methylsulfonyl)phenyl)quinoline

Participants

Reaction Steps

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).

Provenance & Evidence