8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine → 8-Ethyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine

HRID 656902

Reaction equation

HRID 656902 reaction equation
[CH:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)=[CH2:2].[H][H]>CCO.[Pd]>[CH2:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)[CH3:2]

Participants

5

Reactant 2

HCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 671312018-Ethyl-7-fluoro-2-(methyloxy)-1,5-naphthyridineYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine (for a synthesis see WO2004/058144 Example 53(h)) (1.0 g, 4.90 mmol) was stirred in EtOH (50 ml) with 10% palladium on carbon (0.2 g) and the resulting suspension was hydrogenated under 1 atmosphere of hydrogen pressure for 3 h. The mixture was filtered with suction through celite and the solids were washed with MeOH (500 ml). The combined filtrate plus washings were concentrated to give the title compound as a clear oil (1.045 g, 103%).

Workup

  1. filtrationThe mixture was filtered with suction through celite
  2. washthe solids were washed with MeOH (500 ml)
  3. concentrationThe combined filtrate plus washings were concentrated

Sources & evidence

ORD record
ord-8ed8d834b6114c7e9c80179615375876
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Linked notes

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