2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (S)-tert-butyl 2-(7-bromo-6-fluoro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 2-(7-bromo-6-fluoro-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (324 mg, 0.74 mmol) in benzene (7 mL) was added DDQ (185 mg, 0.82 mmol) and the mixture was heated to 80° C. After stirring for 16 h, the reaction mixture was cooled to rt and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (45% to 100% EtOAc/hexanes) to afford (S)-tert-butyl 2-(7-bromo-6-fluoro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (204 mg, 63%).

Provenance & Evidence