Journal
TETRAHEDRON
Volume 66, Issue 14, Pages 2654-2663Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.032
Keywords
3-Alkoxypyrazole; Copper-catalyzed N-arylation; Microwave-assisted synthesis
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Funding
- Medicen initiative [I 06-222/R, I 09-1739/R]
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In the course of a research program focused on the preparation of libraries of new chemical entities derived from 3-alkoxypyrazoles, we studied their N-pyridylation using 2, 3 or 4-bromopyridines This was achieved using Cristau and Taillefer copper-catalyzed arylation method and mostly led to the 3-alkoxy-1H-pyrazol-1-yl pyridine isomer along with lesser amount of the alternative 5-alkoxy-1H-pyrazol-1-yl pyridine The structures of these isomers were often established via their chemical tansformations and sometimes recourse to unambiguous synthetic routes for comparison purposes The alternative use of 2-fluoropyridine-based arylation was also investigated and lifted some of the limitations encountered in the course of this study (C) 2010 Elsevier Ltd All rights reserved
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