Effective and Variable Functionalization of Pyrazolo[1,5-a]pyridines Involving Palladium-Catalyzed Coupling Reactions

Tarek Aboul-Fadl; Stefan Löber; Peter Gmeiner

doi:10.1055/s-2000-8215

Synthesis 2000; 2000(12): 1727-1732
DOI: 10.1055/s-2000-8215

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Effective and Variable Functionalization of Pyrazolo[1,5-a]pyridines Involving Palladium-Catalyzed Coupling Reactions

Tarek Aboul-Fadl^* , Stefan Löber, Peter Gmeiner

^*Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Schuhstr. 19, D-91052 Erlangen, Germany; Fax +49 (91 31) 8 52 25 85; E-mail: gmeiner@pharmazie.uni-erlangen.de

Abstract

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Various 7-substituted pyrazolo[1,5-a]pyridines were synthesized by palladium-mediated cross-coupling reactions. Starting from the corresponding 7-iodo derivatives, incorporation of phenyl, vinyl, ethynyl, cyano, and amino was accomplished. Pyrazolo[1,5-a]pyridine-7-ylzinc iodide could be reacted under Negishi conditions to afford the coupling product 16.

pyrazolo[1,5-a]pyridine - regiodirected metallation - cross coupling - Stille reaction - Suzuki reaction

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