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Synthesis 2021; 53(24): 4709-4722
DOI: 10.1055/s-0037-1610783
DOI: 10.1055/s-0037-1610783
paper
An Expedient Approach to Pyrazolo[3,4-b]pyridine-3-carboxamides via Palladium-Catalyzed Aminocarbonylation
Authors
This work was supported by funding from Eli Lilly and Company (4152 R17825).
Abstract
Pyrazolo[3,4-b]pyridine is a privileged scaffold found in many small drug molecules that possess a wide range of pharmacological properties. Efforts to further develop and exploit synthetic methodologies that permit the functionalization of this heterocyclic moiety warrant investigation. To this end, a series of novel 1,3-disubstituted pyrazolo[3,4-b]pyridine-3-carboxamide derivatives have been prepared by introducing the 3-carboxamide moiety using palladium-catalyzed aminocarbonylation methodology and employing CO gas generated ex situ using a two-chamber reactor (COware®). The functional group tolerance of this optimized aminocarbonylation protocol is highlighted through the synthesis of a range of diversely substituted C-3 carboxamide pyrazolo[3,4-b]pyridines in excellent yields of up to 99%.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610783.
- Supporting Information (PDF) (opens in new window)
Publication History
Received: 02 June 2021
Accepted after revision: 26 July 2021
Article published online:
26 August 2021
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