4-(4-Chlorophenyl)-6-phenyl-2-(prop-2-yn-1-yloxy)nicotinonitrile

We report an efficient and transition-metal-free protocol for the propargylation of 4-(4-chlorophenyl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile using propargyl bromide in the presence of cesium carbonate in dimethylsulfoxide under mild conditions. This synthetic transformation proceeds with marked chemoselectivity, furnishing the O-propargylated pyridine and the N-propargylated 2-pyridone in 75% and 8% yields, respectively. Both products were fully characterized by IR and NMR spectroscopy, as well as high-resolution mass spectrometry, confirming their molecular structures.