Triethylamine → HCID 44574292, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-amino-2-cyanopyridine (2.00 g, 16.8 mmol) in dry dichloromethane (50 mL) was added triethylamine (2.54 g, 25.21 mmol) and the mixture was stirred at 0° C. To the reaction mixture 2-thiophene carbonyl chloride (3.70 g, 25.21 mmol) was added drop wise over a period of 15 minutes, and the reaction mixture was stirred at 0° C. for about 1 hour and then at room temperature overnight. The reaction mixture was diluted with dichloromethane (50 mL) and washed with saturated sodium bicarbonate solution (50 mL) and water (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel, 20-50% ethyl acetate in petroleum ether as an eluent) to obtain N-(6-cyanopyridin-3-yl)thiophene-2-carboxamide (compound 25a) Yield: 0.430 g (7.74%) and N-(6-cyanopyridin-3-yl)-N-(thiophene-2-carbonyl)thiophene-2-carboxamide (compound 25b). Yield: 1.3 g (33.75%).

Provenance & Evidence