209353-23-1Relevant academic research and scientific papers
Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization
Vitaku, Edon,Smith, David T.,Njardarson, Jon T.
supporting information, p. 2243 - 2247 (2016/02/18)
Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.
Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles
Wang, Peng,Farmer, Marcus E.,Huo, Xing,Jain, Pankaj,Shen, Peng-Xiang,Ishoey, Mette,Bradner, James E.,Wisniewski, Steven R.,Eastgate, Martin D.,Yu, Jin-Quan
supporting information, p. 9269 - 9276 (2016/08/05)
Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.
8-Fluoro-6-(methoxymethoxy)quinoline: Synthesis and Regioselective Functionalization via Reaction with Organolithium Compounds
Stadlwieser, Josef,Barbier, Pierre,Taylor, Sven
, p. 1088 - 1094 (2007/10/03)
8-Fluoro-6-(methoxymethoxy)quinoline (1) was synthesized, and the reactivity of 1 against organolithium compounds was studied under different reaction conditions. With BuLi, directed ortho-metalation (DoM) was accompanied by 1,2-addition to the C=N bond.
