4-Fluorophenylboronic acid → 1-ethyl-6-(4-fluorophenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Participants

Reaction Steps

To a mixture of 5-cyano-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-6-yl trifluoromethanesulfonate (253 mg), 4-fluorobenzeneboronic acid (129 mg), powdered potassium phosphonate (195 mg) in 1,4-dioxane (4 ml) was added tetrakis(triphenylphosphine)palladium(0) (18 mg) at room temperature. The mixture was refluxed for 7 hours. Resulting mixture was diluted with EtOAc (10 ml), washed with water (×2) and brine and dried over MgSO4. The solvent was evaporated and the residue was purified with silica gel column chromatography to give 1-ethyl-6-(4-fluorophenyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (175 mg) as colorless solid.

Provenance & Evidence