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Synthesis 2011(16): 2651-2663  
DOI: 10.1055/s-0030-1260110
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Access to 3-Aminoindazoles by Buchwald-Hartwig C-N Coupling Reaction

Elodie Lohou, Valérie Collot*, Silvia Stiebing, Sylvain Rault
CERMN UPRES EA-4258, FR CNRS INC3M, UFR des Sciences Pharmaceutiques, Bd Becquerel, 14032 Caen Cedex, France
Fax: +33(2)31566803; e-Mail: valerie.collot@unicaen.fr ;
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Publication History

Received 21 April 2011
Publication Date:
21 July 2011 (online)

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Abstract

An efficient synthesis of various N-substituted 3-aminoindazoles using Buchwald-Hartwig C-N coupling reaction is described. Several parameters were varied, including the nature of the halogen atom and the protecting group of the starting materials, as well as the effects of the catalyst system, base, solvent, and reaction time. The efficiency of microwave versus conventional heating was also compared to test the outcome of the reaction. Thus, by applying this recent knowledge about metal-catalyzed aminations, an alternative for the direct synthesis of primary 3-aminoindazoles has been provided.

Key words

indazoles - amination - cross-coupling - palladium - copper - microwave promoted amination

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