2-Butanone, 3-bromo- → Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

HRID 427502Notes

Reaction equation

HRID 427502 reaction equation
[NH2:1][C:2]1[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH:15]([CH3:19])[C:16](=O)[CH3:17]>COCCOC>[NH2:1][C:2]1[C:3]2[N:4]([C:15]([CH3:19])=[C:16]([CH3:17])[N:13]=2)[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:12]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 9877541Ethyl 5,6-diaminonicotinate

Product 1

HCID 9942738Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateYield 17.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl 5,6-diaminonicotinate (1.4 g, 7.7 mmol) and 3-bromo-2-butanon (1.16 g, 7.2 mmol) were added to 1,2-dimethoxyethan (50 ml) and refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride. The methylene chloride solution was washed with saturated sodium bicarbonate and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent to give 0.3 g (17%) of the title compound.

Workup

  1. temperaturerefluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThe methylene chloride solution was washed with saturated sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b89a31684d71434fa2939fd30ddbf065
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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