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Synthesis 2011(16): 2651-2663
DOI: 10.1055/s-0030-1260110
DOI: 10.1055/s-0030-1260110
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkDirect Access to 3-Aminoindazoles by Buchwald-Hartwig C-N Coupling Reaction
Weitere Informationen
Received
21 April 2011
Publikationsdatum:
21. Juli 2011 (online)
Publikationsverlauf
Publikationsdatum:
21. Juli 2011 (online)
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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