Bromopinacolone → 6-Bromo-2-tert-butylimidazo[1,2-a]pyridine

HRID 601645Notes

Reaction equation

HRID 601645 reaction equation
Br[CH2:2][C:3](=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1>C(O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:2]=[C:3]([C:4]([CH3:7])([CH3:6])[CH3:5])[N:9]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 21642BromopinacoloneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 231582386-Bromo-2-tert-butylimidazo[1,2-a]pyridineYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-bromopinacolone (178 mg) was dissolved in 2.0 ml of ethanol, 156 mg of 2-amino-5-bromopyridine was added, and the mixture was stirred all night by heating under reflux. After cooled down to room temperature, the solvents were distilled outunder reduced pressure, ethyl acetate followed by saturated sodium hydrogen carbonate aqueous solution were added. Organic layer was dried with anhydrous sodium sulfate, and 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 186 mg of the above compound as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. distillationthe solvents were distilled outunder reduced pressure, ethyl acetate
  4. additionwere added
  5. dry with materialOrganic layer was dried 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-7fc6e1ddfaa341028f309c772b7d2bde
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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