Potassium Carbonate → Ethyl 6-iodo-1-(1-methoxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (Intermediate 24, 1 g, 2.56 mmol) dissolved in THF (10 mL) was added 1-methoxy-3-methylbutan-2-amine hydrochloride (366 mg, 2.38 mmol) followed by potassium carbonate. The reaction mixture was stirred at 60° C. for 2 d. The reaction mixture was concentrated under reduced pressure and the residue was resuspended in DMF (10 mL). Potassium carbonate was added (978 mg, 7.08 mmol), and the reaction mixture was stirred at 70° C. for 2 h. The reaction mixture was cooled down to room temperature and quenched with 1 N HCl. The reaction mixture was partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate, and the organics were dried and concentrated to provide ethyl 6-iodo-1-(1-methoxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (623 mg, 60%).

Provenance & Evidence