Hydrochloric Acid → 2-[2-(4-Pyridin-2-ylphenyl)-2H-tetrazol-5-yl]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[2-(4-bromophenyl)-2H-tetrazol-5-yl]pyridine (300 mg, 1 mmol), 2-pyridylzinc bromide (0.5M in THF, 2 mL) and tetrakis-(triphenylphosphine)palladium(0) (100 mg, 0.085 mmol) in anhydrous THF (10 mL) was degassed for 15 min and heated to 60° C. After 4 hours, a further equivalent of 2- pyridylzinc bromide (0.5M in THF, 2 mL) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was then quenched with brine (25 mL), extracted with EtOAc (3×25 mL), dried over Na2SO4 and concentrated in vacuo. The crude residue was chromotographed on silica gel, eluting with EtOAc to afford a yellow solid. This was dissolved in anhydrous THF (10 mL) and HCl in ether (1.5 equiv) was added and the resulting precipitate was filtered to afford a yellow solid.

Provenance & Evidence