2-Amino-5-methylpyridine → 6-Methyl-2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine

HRID 35518

Reaction equation

HRID 35518 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=3)[N:15]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 153482-Amino-5-methylpyridineHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 28138106-Methyl-2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24 g (0.077 mole) of 1-bromo-2-(4-trifluoromethylphenyl)-2-ethanone, 8.4 g (0.077 mole) of 2-amino-5-methylpyridine and 13 g of sodium bicarbonate are mixed in 210 ml of 95% strength ethanol, and this suspension is heated under reflux until the evolution of gas has ceased. The solvent is then evaporated off under reduced pressure and the evaporation residue is taken up with water and dichloromethane. The organic phase is decanted and dried over magnesium sulphate, and the solvent is removed by evaporation under reduced pressure. The residue is purified by column chromatography.

Workup

  1. temperaturethis suspension is heated
  2. temperatureunder reflux until the evolution of gas
  3. customThe solvent is then evaporated off under reduced pressure
  4. customThe organic phase is decanted
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent is removed by evaporation under reduced pressure
  7. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-a4f089c2a14f4280abf7024273451486
Source dataset
uspto-grants-1988_08
Patent number
US04767755

Linked notes

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