Tetrahydrofuran → 2,6-dichloro-N-(pyridin-3-ylmethyl)pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloronicotinic acid (19.2 g, 0.1 mol), N,N′-carbonyldiimidazole (CDI, 17.8 g, 0.11 mmol) and THF (1 L) was stirred at 60° C. for 30 min and cooled to room temperature. To the mixture was added 3-aminomethylpyridine (10.2 mL, 0.1 mol) and DIEA (21 mL, 0.12 mol). The reaction mixture was stirred at room temperature for 4 hrs, and diluted with EtOAc. The organic layer was washed with H2O, brine, dried over Na2SO4. Concentration of the organic solution gave 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.5 g, 73%). LRMS (M+H+) m/z 282.0; (M+2+H+) m/z 283.9.

Provenance & Evidence