Tetrahedron

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

…, AS Batsanov, MR Bryce, N Saygili, PR Parry, B Tarbit

Index: Thompson, Amy E.; Batsanov, Andrei S.; Bryce, Martin R.; Saygili, Nezire; Parry, Paul R.; Tarbit, Brian Tetrahedron, 2005 , vol. 61, # 21 p. 5131 - 5135

Full Text: HTML

Citation Number: 25

Abstract

This paper describes the commercially-viable synthesis and isolation of 2-ethoxy-3- pyridylboronic acid on a ca. 70g 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 ( ...