General Entry to Pyrazolo[3,4-b]pyridine-3-carboxamides
An Expedient Approach to Pyrazolo[3,4-b]pyridine-3-carboxamides via Palladium-Catalyzed Aminocarbonylation: R. M. Alam, J. J. Keating
Synthesis 2021, 53, DOI: 10.1055/s-0037-1610783
The pyrazolo[3,4-b]pyridine structural unit is present in a large number of biologically active small molecules, including drugs with vasodilatory properties for treating pulmonary hypertension, as well as compounds with anti-cancer and anti-viral activity, along with other pyrazolo[3,4-b]pyridines effective against different neurological disorders. Although there are several methods to access the title structural motif, the synthesis of derivatives carrying a 3-carboxamide substituent is not straightforward, often requiring multi-step sequences. Recently, the group of Professor John J. Keating from the University College Cork (Ireland), reported a novel and expedient entry to 1H-pyrazolo[3,4-b]pyridine-3-carboxamide derivatives, which also features a very broad scope.
Prof. Keating said: “Utilizing a Pd-catalyzed aminocarbonylation strategy, this article showcases an efficient protocol for the synthesis of a wide range of pharmaceutically relevant 1H-pyrazolo[3,4-b]pyridine-3-carboxamide derivatives in high yield (up to 99%).”