Cesium carbonate → Methyl 5-bromo-8-[(4-methoxybenzyl)oxy]-[1,6]-naphthyridine-7-carboxylate

HRID 897341Notes

Reaction equation

HRID 897341 reaction equation
[Br:1][C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 699934-Methyloxybenzyl chloride2×HCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 22346284Methyl 5-bromo-8-[(4-methoxybenzyl)oxy]-[1,6]-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-bromo-8-hydroxy-[1,6]-naphthyridine-7-carboxylate (7.73 g, 27.4 mmol), 4-methoxybenzyl chloride (5.15 g, 32.9 mmol), and Cs2CO3 (10.7 g, 32.9 mmol) in DMF (150 mL) was stirred in an oil bath at 50° C. overnight. Additional quantity of 4-methoxybenzyl chloride (0.6 g), and Cs2CO3 (1 g) was added, and the mixture heated at the same temperature for 8 hour. The resulting mixture was filtered and concentrated under vacuum. The residue was partitioned between dichloromethane and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was dissolved in boiling ethyl acetate (150 mL), hexane was added until solution turn cloudy. The resultant slurry was stirred at room temperature overnight. The solid precipitated was collected by filtration to provide methyl 5-bromo-8-[(4-methoxybenzyl)oxy]-[1,6]-naphthyridine-7-carboxylate.

Workup

  1. temperaturethe mixture heated at the same temperature for 8 hour
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between dichloromethane and brine
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. dissolutionThe residue was dissolved
  10. additionwas added until solution turn cloudy
  11. stirringThe resultant slurry was stirred at room temperature overnight
  12. customThe solid precipitated
  13. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6c92b8f66aa44795a7da0cc783be7802
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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