Réaction #43397

Équation de réaction

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

sodium iodide

→

solid

Rendement 36.0%

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

Rendement 36.0%

Solvants

ethyl acetate

acetone

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureto reflux for 18 hours
3. 3
   AutreThe mixture was evaporated
4. 4
   Autrethe residue partitioned between water (200 ml) and dichloromethane (200 ml)
5. 5
   ExtractionThe aqueous phase was further extracted with dichloromethane (2×200 ml)
6. 6
   Lavagethe combined dichloromethane extracts washed with water (2×200 ml)
7. 7
   Séchagedried over magnesium sulphate
8. 8
   Autreevaporated
9. 9
   AutreThe resulting solid was triturated with ethyl acetate (50 ml)
10. 10
    Filtrationfiltered
11. 11
    Lavagewashed with ethyl acetate (20 ml)
12. 12
    Autreaffording a brown solid
13. 13
    Filtrationfiltered through a plug of silica
14. 14
    AutreEvaporation

Mode opératoire

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%).

Source