Реакция #70458

Уравнение реакции

2-chloro-5-iodopyridine

2-pyrrolidinone

K2CO3

N,N′-dimethyl-1,2-ethanediamine

→

desired product

Выход 103.0%

1-(6-Chloropyridin-3-yl)pyrrolidin-2-one

Выход 103.0%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   ДругоеThe vial is evacuated
2. 2
   Другоеflushed with nitrogen
3. 3
   ТемператураThe reaction mixture was heated
4. 4
   Температураto reflux for 18 h
5. 5
   ФильтрацияThe reaction mixture was filtered through celite and filtrate
6. 6
   Концентрированиеwas concentrated
7. 7
   Другоеto afford the crude material
8. 8
   ДругоеThe mixture was purified by flash chromatography on silica gel
9. 9
   Промывкаeluting with 50-100% EtOAc
10. 10
    workup.ADDITIONFractions containing the desired products
11. 11
    Концентрированиеconcentrated

Методика

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%).

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