铜催化烷氧基吡啶衍生物的三氟甲基化反应。

Copper-Catalyzed Trifluoromethylation of Alkoxypyridine Derivatives.

机构信息

Servier Research Institute of Medicinal Chemistry, Záhony u. 7., H-1031 Budapest, Hungary.

Institute of Chemistry, Eötvös Loránd Unversity, Pázmány Péter s. 1/A, H-1117 Budapest, Hungary.

出版信息

Molecules. 2020 Oct 16;25(20):4766. doi: 10.3390/molecules25204766.

DOI:10.3390/molecules25204766

PMID:33081411

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7587554/

Abstract

The trifluoromethylation of aromatic and heteroaromatic cores has attracted considerable interest in recent years due to its pharmacological relevance. We studied the extension of a simple copper-catalyzed trifluoromethylation protocol to alkoxy-substituted iodopyridines and their benzologs. The trifluoromethylation proceeded smoothly in all cases, and the desired compounds were isolated and characterized. In the trifluoromethylation of 3-iodo-4-methoxyquinoline, we observed a concomitant - methyl migration, resulting in the trifluoromethylated quinolone as a product. Overall, the described procedure should facilitate the broader use of copper-catalyzed trifluoromethylation in medicinal chemistry.

摘要

近年来，由于其药理学相关性，芳基和杂芳基核心的三氟甲基化引起了相当大的关注。我们研究了将简单的铜催化三氟甲基化方案扩展到烷氧基取代的碘吡啶及其苯并类似物。在所有情况下，三氟甲基化都顺利进行，所需的化合物被分离并进行了表征。在 3-碘-4-甲氧基喹啉的三氟甲基化中，我们观察到伴随的 - 甲基迁移，导致三氟甲基化的喹诺酮作为产物。总体而言，所描述的程序应促进铜催化三氟甲基化在药物化学中的更广泛应用。