N,N'-Dimethylethylenediamine → 1-(6-Chloropyridin-3-YL)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of 2-chloro-5-iodopyridine (200 mg, 0.84 mmol) in 4 mL anhydrous dioxane was added 2-pyrrolidinone (60.8 μL, 0.79 mmol), K2CO3 (415.6 mg, 3 mmol), CuI (15.9 mg, 0.084 mmol), and N,N′-dimethyl-1,2-ethanediamine (11.8 μL, 0.083 mmol) in a 2 dram screw-top vial. The vial is evacuated and flushed with nitrogen. The reaction mixture was heated to reflux for 18 h. The reaction mixture was filtered through celite and filtrate was concentrated to afford the crude material. The mixture was purified by flash chromatography on silica gel, eluting with 50-100% EtOAc:heptane. Fractions containing the desired products were combined and concentrated to afford the desired product as a white solid (160 mg, yield: 97.4%).

Provenance & Evidence