2-Butanone, 3-bromo- → 6-Bromo-2,3-dimethylimidazo[1,2-a]pyridin-8-ylamine

HRID 1386085Notes

Reaction equation

HRID 1386085 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Br[CH:11]([CH3:15])[C:12](=O)[CH3:13]>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:11]([CH3:15])=[C:12]([CH3:13])[N:1]=2)[CH:4]=[C:5]([Br:9])[CH:6]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 217173556-Bromo-2,3-dimethylimidazo[1,2-a]pyridin-8-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,3-diamino-5-bromopyridine (4.0 g, 21.29 mmol) and 3-bromo-2-butanone (3.7 g, 24.48 mmol) in ethanol (40 ml) was refluxed overnight. After cooling to room temperature, the crystalline product was filtered and washed with ethanol and ether. The crystals were dissolved in methylene chloride and neutralized by aqueous NaHCO3. The organic layer was separated, dried over Na2SO4 and evaporated in vacuo. Yield 2.3 g.

Workup

  1. filtrationthe crystalline product was filtered
  2. washwashed with ethanol and ether
  3. dissolutionThe crystals were dissolved in methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1c283dadd08b4644ab0a2cb72134620a
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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