Dimethylformamide → 9-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 12-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca 1(14),2,4,10,12-pentaene (11.0 g, 28.7 mmol) in dried DMF (300 mL) was added Pd(PPh3)2Cl2 (1.0 g, 1.4 mmol) and (Me3Si)2NH (14 g, 86 mmol). The mixture was stirred at 70° C. for 4 h under carbon monoxide atmosphere. After removal of the solvent, the residue was treated with ice-water, filtered, extracted with ethyl acetate (400 ml), dried over anhydrous Na2SO4, and concentrated to give 12-bromo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-4-carboxamide (7.2 g, 97% yield), which was used in the next step without further purification. LCMS (ESI) m/z: 308.1 [M+H+].

Provenance & Evidence