Sodium Cyanide → 2-(5,6-Dichloropyridin-2-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(bromomethyl)-2,3-dichloropyridine (Preparation 60, 2.90 g, 3.13 mmol) in IMS (20 mL) and water (15 mL) was added NaCN (552 mg, 11.3 mmol). The reaction was heated to 100° C. for 1 hour before cooling to room temperature and quenching with saturated aqueous NaHCO3 solution (50 mL). The mixture was extracted with DCM (3×50 mL) and the organic layers combined, dried over MgSO4 and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-100% MeCN in water with 0.1% formic acid to afford the title compound (341 mg, 15% over two steps).

Provenance & Evidence