Reacción #43397

Ecuación de reacción

8-[1-(chloromethyl)ethenyl]-7-fluoro-2-(methyloxy)-1,5-naphthyridine

sodium iodide

→

solid

Rendimiento 36.0%

3-Fluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Rendimiento 36.0%

Disolventes

ethyl acetate

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux for 18 hours
3. 3
   OtroThe mixture was evaporated
4. 4
   Otrothe residue partitioned between water (200 ml) and dichloromethane (200 ml)
5. 5
   ExtracciónThe aqueous phase was further extracted with dichloromethane (2×200 ml)
6. 6
   Lavadothe combined dichloromethane extracts washed with water (2×200 ml)
7. 7
   Secadodried over magnesium sulphate
8. 8
   Otroevaporated
9. 9
   OtroThe resulting solid was triturated with ethyl acetate (50 ml)
10. 10
    Filtraciónfiltered
11. 11
    Lavadowashed with ethyl acetate (20 ml)
12. 12
    Otroaffording a brown solid
13. 13
    Filtraciónfiltered through a plug of silica
14. 14
    OtroEvaporation

Procedimiento

A mixture of 8-[1-(chloromethyl)ethenyl]-7-fluoro-2-(methyloxy)-1,5-naphthyridine (4.9 g, 19.5 mmol) and sodium iodide (29 g, 195 mmol) in acetone (100 ml) was heated to reflux for 18 hours. The mixture was evaporated and the residue partitioned between water (200 ml) and dichloromethane (200 ml). The aqueous phase was further extracted with dichloromethane (2×200 ml) and the combined dichloromethane extracts washed with water (2×200 ml) dried over magnesium sulphate and evaporated. The resulting solid was triturated with ethyl acetate (50 ml) and filtered and washed with ethyl acetate (20 ml) affording a brown solid. This material was then dissolved in ethyl acetate and filtered through a plug of silica. Evaporation afforded a solid (1.4 g, 36%).

Fuente