1-Bromo-2-butanone → 6-Bromo-2-ethylimidazo[1,2-a]pyridine

HRID 601666Notes

Reaction equation

HRID 601666 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH3:5].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1>C(O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([CH:2]=[C:3]([CH2:4][CH3:5])[N:7]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 231582656-Bromo-2-ethylimidazo[1,2-a]pyridineYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 1-bromo-2-butanone was dissolved in 80 ml of ethanol, 5.71 g of 2-amino-5-bromopyridine was added, and the mixture was stirred all night by heating under reflux. After cooling down to room temperature, the solvents were distilled outunder reduced pressure, and ethyl acetated followed by saturated sodium bicarbonate aqueous solution were added. After drying organic layer with anhydrous sodium sulfate, the solvents were distilled outunder reduced pressure. The obtained residues were purified by preparative thin-layer silicagel chromatography (hexane:ethyl acetate=75:25), to obtain 4.82 g of the above compound as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. distillationthe solvents were distilled outunder reduced pressure, and ethyl
  4. additionwere added
  5. dry with materialAfter drying organic layer with anhydrous sodium sulfate
  6. distillationthe solvents were distilled outunder reduced pressure
  7. customThe obtained residues were purified by preparative thin-layer silicagel chromatography (hexane:ethyl acetate=75:25)

Sources & evidence

ORD record
ord-abd7cd04bb6643c68ca00741e741bc78
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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