Sodium Bicarbonate → Methyl 6-(methyloxy)-1,5-naphthyridine-3-carboxylate

HRID 656919Notes

Reaction equation

HRID 656919 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15].C([O-])(O)=O.[Na+].[H][H]>CO.O1CCOCC1.[Pd]>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:2]2

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 68817384Methyl 4-bromo-6-(methyloxy)-1,5-naphthyridine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68817307Methyl 6-(methyloxy)-1,5-naphthyridine-3-carboxylateYield 96.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of methyl 4-bromo-6-(methyloxy)-1,5-naphthyridine-3-carboxylate (1.67 g, 5.64 mmol)) and NaHCO3 (0.84 g, 10 mmol) in MeOH (20 ml) and 1,4-dioxane (15 ml) was added 10% Pd/C (0.75 g) and the mixture was then stirred at rt under 1 atmosphere of hydrogen for 3 h. The reaction mixture was then filtered through a thin pad of Celite, washing through with EtOH. The filtrate was evaporated and stirred in 50 ml of water, the solid was then filtered off and dried in vacuo to give the desired product (1.19 g, 96%).

Workup

  1. filtrationThe reaction mixture was then filtered through a thin pad of Celite
  2. washwashing through with EtOH
  3. customThe filtrate was evaporated
  4. filtrationthe solid was then filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c7c3825cc9c54cba81d449bf891bfbbb
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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