Picolinic acid → N-(2-Bromoethyl)pyridine-2-carboxamide

Participants

Reaction Steps

Picolinic acid (0.99 g) in dichloromethane (30 mL) was treated with triethylamine (1.27 mL) and HATU (3.6 g). The mixture was stirred for 10 minutes then a solution of 2-bromoethylamine hydrobromide (1.5 g) and triethylamine (1.27 mL) in dichloromethane (20 mL) was added. The reaction mixture was stirred for 3h. Water (50 mL) was added and the layers were separated. The organic layer was washed with water (3×50 mL), dried over magnesium sulphate and evaporated to afford the crude product which was purified by silica gel chromatography eluting with 0-100% EtOAc/dichloromethane. The relevant fractions were combined and evaporated, dissolved up in EtOAc (40 mL) and washed with saturated sodium hydrogen carbonate solution, ensuring the aqueous layer remained basic. The organic layer was dried over magnesium sulphate and evaporated to give the sub-titled compound (0.88 g) as a white solid.

Provenance & Evidence