Acetic Acid → HCID 86671547, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (110 μL, 0.77 mmol, 2.0 eq) is added at 0° C. to a stirred solution of 6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene-3-carboxylic acid (100 mg, 0.39 mmol, 1.0 eq) in tetrahydrofuran (10 mL), followed by ethyl chloroformate (73 μL, 0.77 mmol, 2.0 eq). After 1 hour stirring at 0° C., a solution of diazomethane in diethyl ether (20 mL, freshly prepared) is added at 0° C. to the reaction mixture. After 2 hours stirring at 0° C., a 33% hydrobromic acid solution in acetic acid (200 μL, 1.16 mmol, 3.0 eq) is added at 0° C. to the reaction mixture. After 1 hour stirring at 0° C., solvent is removed to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 3:1, v/v) to afford 2-bromo-1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-ethanone as a light yellow oil (33 mg, 25% yield)

Provenance & Evidence