Potassium Phosphate, Tribasic → 6-(4-(3-hydroxypropyl)-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1.29 g), 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenyl)propan-1-ol (2.432 g), tris(dibenzylideneacetone)dipalladium (0.307 g), tricyclohexylphosphine (0.225 g) and potassium phosphate (2.417 g) were suspended in dioxane (20 ml) and water (8 ml). The reaction mixture was placed under a nitrogen atmosphere and heated to reflux (110° C.) for 1.5 hours. The mixture was allowed to cool to room temperature then diluted with EtOAc (500 mL), filtered through celite and washed with water (200 mL). Organic layer was dried over sodium sulphate and solvent was evaporated under reduced pressure. The solid residue was washed with ether to afford 6-[4-(3-hydroxypropyl)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1.5 g).

Provenance & Evidence