Hydrogen Peroxide → 2-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine-5-oxide

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Reaction Steps

To a solution of 2-(2,6-dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine (5.3 g, 12.6 mmol) in DCM (100 mL) under a nitrogen atmosphere was added methyltrioxorhenium(VII) (313 mg, 1.3 mmol) followed by 30% aqueous hydrogen peroxide (2.6 mL, 25.1 mmol). The reaction mixture was stirred at room temperature for 48 hours with a further two additions of methyltrioxorhenium(VII) (313 mg, 1.3 mmol) and 30% aqueous hydrogen peroxide (2.6 mL, 25.1 mmol) added over this period. The precipitate obtained was collected by filtration and the filtrate was partitioned between water. The aqueous layer was extracted with DCM (×2). The combined organic phases were washed with a saturated solution of NaHCO3, dried (MgSO4) and concentrated under reduced pressure. The resultant residue was combined with the previously filtered solid and was purified by column chromatography on silica gel eluting with 0-90% EtOAc in petroleum ether (40-60° C.), followed by 0-10% MeOH in DCM to afford the title compound as a white solid (2.5 g, 45% yield). LCMS (Method D): RT=3.36 min, m/z: 441 [M+H+].

Provenance & Evidence