Water → Ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate

HRID 2356308Notes

Reaction equation

HRID 2356308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[N:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].P(Br)(Br)[Br:20].O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Br:20])=[N:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 600736Ethyl 4-hydroxy-6-methoxy-1,5-naphthyridine-3-carboxylate

Product 1

HCID 68454651Ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-methoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (74.57 g, 300 mmol) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately room temperature—may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmol) was added dropwise over 15 min and stirring was continued for an additional 30 min. Water (1 L) was added, followed by saturated sodium carbonate solution to pH 7. The solid was collected by suction filtration, washed with water and dried under vacuum over phosphorus pentoxide to give the title compound (83.56 g, 90%).

Workup

  1. temperatureto maintain approximately room temperature—
  2. temperaturecooling on a large scale)
  3. stirringstirring
  4. filtrationThe solid was collected by suction filtration
  5. washwashed with water
  6. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-793d376025b8433aa578fe05619b0cf6
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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