Iodine → HCID 178452582, compound

Participants

Reaction Steps

To a stirred ice-cooled solution of {1-[4-(6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (52 mg, 0.10 mmol) in DMF (0.5 mL), was added powdered potassium hydroxide (45 mg, 0.80 mmol). After 3 min, a solution of iodine (102 mg, 0.40 mmol) in DMF (0.5 mL) was added. The resulting mixture was stirred at RT for 16 hours. Aqueous sodium thiosulfate was added and the mixture was extracted twice with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 30 to 75% EtOAc in cyclohexane) to afford the title compound (4.2 mg, 7%) as a white solid. LCMS (Method H): RT=4.39 min, [M+H]+=634.

Provenance & Evidence