Tetrahedron

Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals …

T Verdelet, G Mercey, N Correa, L Jean, PY Renard

Index: Verdelet, Tristan; Mercey, Guillaume; Correa, Nobi; Jean, Ludovic; Renard, Pierre-Yves Tetrahedron, 2011 , vol. 67, # 45 p. 8757 - 8762

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Citation Number: 15

Abstract

A practical and rapid preparation of 3-benzyloxy-4-bromo and 3-benzyloxy-5- bromopicolinate esters 10 and 16 was developed in four steps, respectively, in 38% and 31% overall yield. Then their viability as partners for cross-coupling reactions has been evaluated in Suzuki–Miyaura, Hartwig–Buchwald, and Sonogashira reactions to synthesize biologically relevant targets. The preparation of these two highly functionalizable pyridines ...