Cyclohexylamine → Ethyl 6-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 66, 1.14 g, 3.29 mmol, 1 equiv.) in DMF (6.5 mL) was added cyclohexanamine (592 mg, 3.29 mmol, 1 equiv.). This reaction mixture was stirred at 70° C. for 30 min. Potassium carbonate (1.36 g, 9.86 mmol, 3 equiv.) was added and stirred at 70° C. for 2 h. The reaction mixture was cooled to room temperature and quenched with water (2 mL). 1 N HCl was added until pH 4-5 was reached. The precipitate was washed with water and hexanes and dried to provide ethyl 6-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate (1.15 g, 92%).

Provenance & Evidence