Sodium Iodide → 3,8-Difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15136Notes

Reaction equation

HRID 15136 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:6]([F:18])=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([O:15]C)[C:11]([F:17])=[CH:10]2)=[CH2:4].[I-].[Na+]>C(#N)C>[F:18][C:6]1[CH:7]=[N:8][C:9]2[CH:10]=[C:11]([F:17])[C:12](=[O:15])[N:13]3[CH2:2][C:3](=[CH2:4])[C:5]=1[C:14]=23

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 675271518-[1-(Chloromethyl)ethenyl]-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

Product 1

HCID 675274023,8-Difluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-[1-(chloromethyl)ethenyl]-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine (320 mg, 1.18 mmol) and sodium iodide (885 mg) in acetonitrile (20 ml) was heated to reflux for 20 hours. The cooled mixture was evaporated then diluted with water and extracted with dichloromethane. The organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica eluting with a gradient of 0-100% ethyl acetate in hexane affording product (168 mg, 65%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. customThe cooled mixture was evaporated
  4. additionthen diluted with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic extracts were dried over magnesium sulphate
  7. customevaporated
  8. customThe residue was chromatographed on silica eluting with a gradient of 0-100% ethyl acetate in hexane affording product (168 mg, 65%)

Sources & evidence

ORD record
ord-11ca716ac08e4600a5bb41b61801ea94
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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