A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines

Herein
is reported the design and application of a reagent for
the direct functionalization of pyridines. These reactions occur under
mild conditions and exhibit broad functional group tolerance, enabling
the late-stage functionalization of drug-like molecules. The reagent
can be easily prepared on large scale from inexpensive reagents, and
reacts in the title reaction with acetonitrile, sodium chloride, and
sodium methanesulfonate as the sole byproducts. Although this Communication
focuses primarily on reactions with cyanide as nucleophile, preliminary
experiments with other nucleophiles foreshadow the broad reaching
synthetic utility of this approach.