Synthesis and cross coupling of a highly substituted 2-pyridylboronate: application to the large scale synthesis of a mineralocorticoid antagonist

The large scale synthesis of functionalized 2-pyridylboronate 8 and optimization of its Suzuki–Miyaura coupling to chloropyrazoline (R)-7 to provide a scalable synthesis of mineralocorticoid antagonist (R)-1 is described.

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Bibliographic Details
Published in:Tetrahedron letters 2011-12, Vol.52 (52), p.7025-7029
Main Authors: Boos, Charles, Bowles, Daniel M., Cai, Cuiman, Casimiro-Garcia, Agustin, Chen, Xiangyang, Hulford, Catherine A., Jennings, Sandra M., Jason Kiser, E., Piotrowski, David W., Sammons, Matthew, Wade, Robert A.
Format: Article
Language:English
Subjects:
2-Pyridylboronate
Chemistry
Cross coupling
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Joining
Large-scale synthesis
Optimization
Organic chemistry
Preparations and properties
Pyrazoline
Suzuki–Miyaura coupling
Synthesis (chemistry)
Tetrahedrons
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Description
Summary:The large scale synthesis of functionalized 2-pyridylboronate 8 and optimization of its Suzuki–Miyaura coupling to chloropyrazoline (R)-7 to provide a scalable synthesis of mineralocorticoid antagonist (R)-1 is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.10.052