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

HRID 1820663Notes

Reaction equation

HRID 1820663 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 mmole) in dry DMF (260 mL) under argon was stirred efficiently* in a water bath (to maintain approximately RT—may need slight ice-cooling on a large scale). Phosphorus tribromide (30.0 mL, 316 mmole) 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 RT—
  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-a9c592813d6648de911cebbac813c54b
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Reaction notes

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