3-Cyanopyridine → 6-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromopyridin-2-amine (2 g, 11.6 mmol), nicotinonitrile (24.1 g, 231 mmol), 1,10-phenanthroline monohydrate (115 mg, 578 μmol) and copper (I) bromide (82.9 mg, 578 μmol) was placed in a 100 ml 2 necked flask and heated to 135° C. Heating was continued while air was bubbled gently through the mixture for 1.5 days. The excess nicotinonitrile was distilled off under reduced pressure and the black residue purified by chromatography (70 g silicagel column using heptane/ethyl acetate 10-100% as eluent). Final evaporation of the solvents afforded 6-bromo-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine (1.66 g, 52%) as yellow solid. Mp.: 176° C. MS: m/z=275/277 (M+H+).

Provenance & Evidence