98273-59-7Relevant articles and documents
High-Throughput Screening, Discovery, and Optimization to Develop a Benzofuran Class of Hepatitis C Virus Inhibitors
He, Shanshan,Jain, Prashi,Lin, Billy,Ferrer, Marc,Hu, Zongyi,Southall, Noel,Hu, Xin,Zheng, Wei,Neuenswander, Benjamin,Cho, Chul-Hee,Chen, Yu,Worlikar, Shilpa A.,Aubé, Jeffrey,Larock, Richard C.,Schoenen, Frank J.,Marugan, Juan J.,Liang, T. Jake,Frankowski, Kevin J.
, p. 641 - 652 (2015)
Using a high-throughput, cell-based HCV luciferase reporter assay to screen a diverse small-molecule compound collection (300 000 compounds), we identified a benzofuran compound class of HCV inhibitors. The optimization of the benzofuran scaffold led to t
Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source
Wu, Zhuo,Wei, Feng,Wan, Bin,Zhang, Yanghui
, p. 4524 - 4530 (2021/05/04)
A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.
Deprotonative Metalation of Methoxy-Substituted Arenes Using Lithium 2,2,6,6-Tetramethylpiperidide: Experimental and Computational Study
Akimoto, Gaku,Otsuka, Mai,Takita, Ryo,Uchiyama, Masanobu,Hedidi, Madani,Bentabed-Ababsa, Ghenia,Lassagne, Frédéric,Erb, William,Mongin, Florence
, p. 13498 - 13506 (2018/11/20)
The reaction pathways of lithium 2,2,6,6-tetramethylpiperidide (LiTMP)-mediated deprotonative metalation of methoxy-substituted arenes were investigated. Importantly, it was experimentally observed that, whereas TMEDA has no effect on the course of the reactions, the presence of more than the stoichiometric amount of LiCl is deleterious, in particular without an in situ trap. These effects were corroborated by the DFT calculations. The reaction mechanisms, such as the structure of the active species in the deprotonation event, the reaction pathways by each postulated LiTMP complex, the stabilization effects by in situ trapping using zinc species, and some kinetic interpretation, are discussed herein.