An Orthogonal Synthetic Approach to Nonsymmetrical Bisazolyl 2,4,6-Trisubstituted Pyridines

Abstract

A three-step synthetic route giving access to nonsymmetrical bisazolyl 2,4,6-trisubstituted pyridines with different substituents on the pyrazole, indazole, and pyridine heterocycles is described. From the readily available 4-bromo-2,6-difluoropyridine, both fluorine atoms allow for easy selective stepwise substitution, and the bromine atom provides easy access to additional functionalities through both Suzuki and Sonogashira Pd(0) cross-coupling reactions. These synthons represent optimal structures as building blocks in complexation and metalloorganic structures for the tuning of their chelating and photophysical properties.

Keywords

• pyrazolylpyridines
• indazolylpyridines
• nucleophilic substitution
• C–C coupling