Reaction #1005965

Reaction equation

2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine

2-ethylsulfanylphenylboronic acid pinacol ester

tricyclohexylphosphine

tripotassium phosphate

→

2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine

Yield 89.1%

Solvents

water

1,4-dioxane

water

Ethyl acetate

Conditions

Workup

1. 1
   Filtrationthe mixture was filtered
2. 2
   ExtractionThe aqueous layer of the filtrate was extracted with ethyl acetate
3. 3
   Washthe mixture was washed with water
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   ConcentrationThe mixture was concentrated under reduced pressure

Procedure

A mixture of 526 mg of 2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine, 576 mg of 2-ethylsulfanylphenylboronic acid pinacol ester, 50 mg of tris(dibenzylideneacetone) dipalladium(0), 201 mg of tricyclohexylphosphine (18% toluene solution), 1.26 g of tripotassium phosphate, 4.5 ml of 1,4-dioxane and 1.5 ml of water was stirred at 100° C. for 2.5 hours. Ethyl acetate and water were poured to the cooled reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, then combined with the organic layer of the filtrate, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 570 mg of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 4).

Source