1365828-08-5Relevant academic research and scientific papers
Palladium-Catalyzed C-H/C-H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1 H-Indazoles
Yu, Jingbo,Yang, Xinjie,Wu, Chongyang,Su, Weike
, p. 1009 - 1021 (2020)
C3-alkenylated and C3-(hetero)arylated 1H-indazoles are privileged structural motifs in numerous pharmaceuticals. Direct C3-alkenylation and C3-(hetero)arylation of 1H-indazoles have been significantly challenging because of the inert nature of this carbon center. Herein, we present an efficient mechanochemical strategy for palladium-catalyzed C-H/C-H cross-coupling to construct C3-alkenylated and C3-heteroarylated 1H-indazoles using low-cost copper oxidants with satisfactory product yields and broad functional group tolerance. The robustness of the developed protocols was further demonstrated by the unprecedented total mechanosynthesis of the intermediate of PLK4 inhibitor CFI-400945 and HIF-1α inhibitor YC-1.
Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib
Yu, Jingbo,Hong, Zikun,Yang, Xinjie,Jiang, Yu,Jiang, Zhijiang,Su, Weike
supporting information, p. 786 - 795 (2018/04/16)
A mechanically-activated chemoselective Heck coupling for the synthesis of 3-vinylindazoles has been developed with the aid of catalytic amounts of TBAB and NaBr as both dehalogenation restrainer and grinding auxiliary. After tuning of the chemical conditions and mechanical parameters, a series of non-activated 3-bromoindazoles and a broad scope of olefins worked well to give the corresponding coupling products in good to excellent yields. A further application of this protocol was performed in a two-step mechanochemical Heck/Migita cross coupling, which provided a highly efficient route for the synthesis of axitinib.
One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation
Markina, Nataliya A.,Dubrovskiy, Anton V.,Larock, Richard C.
supporting information; experimental part, p. 2409 - 2412 (2012/04/11)
The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl)aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-
