2-Bromo-4'-methylacetophenone → 2-(p-Tolyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine

HRID 35516

Reaction equation

HRID 35516 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=O>C(O)CC>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[N:1]=[C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]3[CH:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 139380372-(p-Tolyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridineYield 70.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

10 g (0.0616 mole) of 2-amino-5-trifluoromethylpyridine and 17.5 g (0.0616 mole) of 1-bromo-2-(4-methylphenyl)-2-ethanone are mixed in 200 ml of n-propanol and the solution is heated to reflux. At the end of the reaction, the reaction mixture is concentrated under reduced pressure and the evaporation residue taken up with water and treated with an excess of ammonia solution until the pH is basic. The imidazopyridine is extracted with dichloromethane and purified by chromatography. 11.95 g (56%) of white solid are obtained. M.p. 187°-188° C.

Workup

  1. temperaturethe solution is heated to reflux
  2. customAt the end of the reaction
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. additiontreated with an excess of ammonia solution until the pH
  5. extractionThe imidazopyridine is extracted with dichloromethane
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-20bd24ff2e884f868dd93e00939014f6
Source dataset
uspto-grants-1988_08
Patent number
US04767755

Linked notes

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