Potassium Carbonate → 2-Phenylpyridine-3-carbonitrile

Participants

Reaction Steps

To a solution of 2-chloro-3-cyanopyridine (4.06 g, 29.3 mmol) in toluene (60 mL) was added phenylboronic acid (5.4 g, 43.9 mmol), potassium carbonate (6.1 g, 44.1 mmol) and tetrakis(triphenylphosphine)palladium (1.7 g, 1.5 mmol). The mixture was refluxed under nitrogen for 24 hours, then the solvent was removed under reduced pressure. The residue was purified on a silica gel column using 100% CH2Cl2 then 99:1 CH2Cl2:MeOH as mobile phase. Pure fractions were combined and dried in vacuo to yield the solid 2-phenyl-3 cyanopyridine (5.0 g, HPLC RT=2.98 min, method A; LC-MS m/z=181).

Provenance & Evidence