Hydrogen Peroxide → 3,3,5-Trifluoro-1H,2H,3H-pyrrolo[2,3-b]pyridin-2-one

Participants

Reaction Steps

Hydrogen peroxide (30% aqueous solution, 0.984 mL, 9.63 mmol) was added dropwise to a stirred mixture of 2-amino-5-fluoropyridine (0.540 g, 4.82 mmol), ferrocene (0.090 g, 0.482 mmol), and ethyl bromodifluoroacetate (1.862 mL, 14.45 mmol) in DMSO (24 mL) under an argon atmosphere. The mixture was stirred at room temperature for 18 h. Sulfuric acid (0.514 mL, 9.63 mmol) was added, and the reaction mixture was stirred at room temperature for another 24 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.248 g, 1.318 mmol, 27.4% yield) as a brown solid. M+1: 189.1.

Provenance & Evidence