Reaction #1005972

Reaction equation

2-bromo-2′-ethylsulfonylacetophenone

2-amino-4-trifluoromethylpyridine

→

2-(2-ethylsulfonylphenyl)-7-trifluoromethyl-imidazo[1,2-a]pyridine

Yield 26.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas refluxed for 1 hour
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   workup.ADDITIONA mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF
4. 4
   workup.ADDITIONWater was poured to the cooled reaction mixture
5. 5
   Extractionthe mixture was extracted with ethyl acetate
6. 6
   WashThe organic layer was washed with water
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

A mixture of 1.0 g of 2-bromo-2′-ethylsulfonylacetophenone, 334 mg of 2-amino-4-trifluoromethylpyridine and 4 ml of ethanol was refluxed for 1 hour and concentrated under reduced pressure. A mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF was stirred at 130° C. for 1 hour. Water was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 190 mg of 2-(2-ethylsulfonylphenyl)-7-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 8).

Source