3-Aminopyridine → 5-Iodo-N-(pyridin-3-yl)-6-(2,2,2-trifluoroethoxy)nicotinamide

Participants

Reaction Steps

5-Iodo-6-(2,2,2-trifluoroethoxy)nicotinic acid (1 g, 2.88 mmol) was dissolved in DMF (10.0 mL); 3-amino-pyridine (285 mg, 3.03 mmol), TBTU (981 mg, 3.05 mmol) and N,N-diisopropylethylamine (1.8 g, 14.4 mmol) were added and the reaction mixture was stirred for 20 hours. The mixture was poured into 5 mL 1 M NaOH solution and extracted with i-propyl acetate (2×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give a light yellow solid. Crystallization from dichloromethane afforded the title compound (0.78 g, 64%) as white solid; MS (ESI) 423.9 (M+H)+.

Provenance & Evidence