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Synthesis 2021; 53(24): 4709-4722
DOI: 10.1055/s-0037-1610783
paper

An Expedient Approach to Pyrazolo[3,4-b]pyridine-3-carboxamides via Palladium-Catalyzed Aminocarbonylation

Ryan M. Alam 
a   Analytical & Biological Chemistry Research Facility (ABCRF), University College Cork, Cork T12 YN60, Ireland
b   School of Chemistry, Kane Building, University College Cork, Cork T12 YN60, Ireland
,
John J. Keating  ∗
a   Analytical & Biological Chemistry Research Facility (ABCRF), University College Cork, Cork T12 YN60, Ireland
b   School of Chemistry, Kane Building, University College Cork, Cork T12 YN60, Ireland
c   School of Pharmacy, Pharmacy Building, University College Cork, Cork T12 YN60, Ireland
› InstitutsangabenThis work was supported by funding from Eli Lilly and Company (4152 R17825).
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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%.

Key words

pyrazolo[3,4-b]pyridine - 7-azaindazole - palladium - aminocarbonylation - carboxamide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610783.
  • Supporting Information


Publikationsverlauf

Eingereicht: 02. Juni 2021

Angenommen nach Revision: 26. Juli 2021

Artikel online veröffentlicht:
26. August 2021

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