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

HRID 15119Notes

Reaction equation

HRID 15119 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:6]([F:17])=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([O:15]C)[CH:11]=[CH:10]2)=[CH2:4].[I-].[Na+]>CC(C)=O.C(OCC)(=O)C>[F:17][C:6]1[CH:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12](=[O:15])[N:13]3[CH2:2][C:3](=[CH2:4])[C:5]=1[C:14]=23

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 675271068-[1-(Chloromethyl)ethenyl]-7-fluoro-2-(methyloxy)-1,5-naphthyridine

Product 1

HCID 675275493-Fluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneYield 36%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customThe mixture was evaporated
  4. customthe residue partitioned between water (200 ml) and dichloromethane (200 ml)
  5. extractionThe aqueous phase was further extracted with dichloromethane (2×200 ml)
  6. washthe combined dichloromethane extracts washed with water (2×200 ml)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe resulting solid was triturated with ethyl acetate (50 ml)
  10. filtrationfiltered
  11. washwashed with ethyl acetate (20 ml)
  12. customaffording a brown solid
  13. filtrationfiltered through a plug of silica
  14. customEvaporation

Sources & evidence

ORD record
ord-ee63a2089abf409798a823d503d81383
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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