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

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%).

1. customThe vial is evacuated
2. customflushed with nitrogen
3. temperatureThe reaction mixture was heated
4. temperatureto reflux for 18 h
5. filtrationThe reaction mixture was filtered through celite and filtrate
6. concentrationwas concentrated
7. customto afford the crude material
8. customThe mixture was purified by flash chromatography on silica gel
9. washeluting with 50-100% EtOAc
10. additionFractions containing the desired products
11. concentrationconcentrated

ORD record

ord-6b923c2f957b4a1c8a9cd3883d749232

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536168B2