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

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.

Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles

“…This work began with a literature review to identify the best conditions for this kind of transformation. Once we had collected the main and most commonly used reaction conditions for the Buchwald-Hartwig coupling reaction, [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] we selected the conditions that mainly applied to the heterocycles frequently used by the team. The following conditions were identified as the starting point of this study ( Table 1).…”