C–H Arylation in the Formation of a Complex Pyrrolopyridine, the Commercial Synthesis of the Potent JAK2 Inhibitor, BMS-911543

The development of an improved short and efficient commercial synthesis of the JAK2 inhibitor, a complex pyrrolopyridine, BMS-911543, is described. During the discovery and development of this synthesis, a Pd-catalyzed C–H functionalization was invented which enabled the rapid union of the key pyrro...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-04, Vol.84 (8), p.4661-4669
Main Authors: Fox, Richard J, Cuniere, Nicolas L, Bakrania, Lopa, Wei, Carolyn, Strotman, Neil A, Hay, Michael, Fanfair, Dayne, Regens, Christopher, Beutner, Gregory L, Lawler, Michael, Lobben, Paul, Soumeillant, Maxime C, Cohen, Benjamin, Zhu, Keming, Skliar, Dimitri, Rosner, Thorsten, Markwalter, Chester E, Hsiao, Yi, Tran, Kristy, Eastgate, Martin D
Format: Article
Language:English
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Summary:The development of an improved short and efficient commercial synthesis of the JAK2 inhibitor, a complex pyrrolopyridine, BMS-911543, is described. During the discovery and development of this synthesis, a Pd-catalyzed C–H functionalization was invented which enabled the rapid union of the key pyrrole and imidazole fragments. The synthesis of this complex, nitrogen-rich heterocycle was accomplished in only six steps (longest linear sequence) from readily available materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02383