HCID 86687720, compound → HCID 86687732, compound

Participants

Reaction Conditions

Reaction Steps

A RBF was charged with perfluorophenyl 1-(5-chloro-2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (1.25 g, 2.35 mmol). The reaction was purged with N2. Then ethyl acetate (23.5 mL) was added followed by palladium, 10 wt % on activated carbon (0.749 g, 0.704 mmol). The flask was evacuated and back filled with N2 (3×). The flask was evacuated again and then pressurized with hydrogen to 42 PSI. The reaction was heated to 75° C. After 2 d, LCMS showed 92:8 ratio of product:SM. The reaction was cooled to rt and filtered through a pad of Celite with the aid of EtOAc. The filtrate was concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (80 g), eluting with a gradient of 0% to 30% EtOAc in heptane, to provide perfluorophenyl 1-(2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (613 mg, 52.4% yield) as off-white solid. m/z (ESI) 499.0 (M+H)+.

Provenance & Evidence