Here we report the first synthesis of a family of novel heterocyclic compounds based on a 5-dihydropyrazolo[3',4':5,6]pyrano[3,4- b]pyridine core. In the course of our drug discovery programs, we had need to access the previously unknown 5-dihydropyrazolo[3',4':5,6]pyrano[3,4- b]pyridine core. Initial attempts required long reaction times, which led to degradation and side products. Reaction optimization identified a Pd-catalyzed, microwave-assisted C-H heteroarylation protocol for the rapid, general, and high yielding synthesis of this tricyclic core (as well as related analogs) suitable to drive optimization efforts.
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