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2-Ethoxy-3-pyridylboronic acid: A versatile reagent for the synthesis of highly-functionalised 3-aryl/heteroaryl-pyridines via Suzuki cross-coupling reactions

Thompson, A.E.; Batsanov, A.S.; Bryce, M.R.; Saygili, N.; Parry, P.R.; Tarbit, B.

Authors

A.E. Thompson

A.S. Batsanov

N. Saygili

P.R. Parry

B. Tarbit



Abstract

This paper describes the commercially-viable synthesis and isolation of 2-ethoxy-3-pyridylboronic acid on a ca. 70 g scale via a directed ortho-metalation reaction on readily-available 2-ethoxypyridine. A range of efficient cross-coupling reactions of 2-ethoxy-3-pyridylboronic acid with selected aryl/heteroaryl halides under palladium-catalysed Suzuki-Miyaura conditions yield novel 2-ethoxy-3-aryl/heteroaryl-pyridines in high yield (heteroaryl=pyridyl, pyrimidyl, pyrazyl). The X-ray crystal structure of 2-ethoxy-3-pyridylboronic acid reveals that the boronic acid group takes part in an intramolecular O-(HO)-O-... bond with the adjacent ethoxy substituent, and an intermolecular O-(HN)-N-... bond. (c) 2005 Elsevier Ltd. All rights reserved.

Citation

Thompson, A., Batsanov, A., Bryce, M., Saygili, N., Parry, P., & Tarbit, B. (2005). 2-Ethoxy-3-pyridylboronic acid: A versatile reagent for the synthesis of highly-functionalised 3-aryl/heteroaryl-pyridines via Suzuki cross-coupling reactions. Tetrahedron, 61(21), 5131-5135

Journal Article Type Article
Publication Date 2005-05
Journal Tetrahedron
Print ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 61
Issue 21
Pages 5131-5135