Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents

[Image: see text] We herein report the use of phenyl trimethylammonium iodide (PhMe(3)NI) as a safe, nontoxic, and easy-to-handle reagent for an absolutely monoselective N-methylation of amides and related compounds as well as for the N-methylation of indoles. In addition, we expanded the method to...

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Detalles Bibliográficos
Autores principales: Templ, Johanna, Gjata, Edma, Getzner, Filippa, Schnürch, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9578047/
https://www.ncbi.nlm.nih.gov/pubmed/36190781
http://dx.doi.org/10.1021/acs.orglett.2c02766
Descripción
Sumario:[Image: see text] We herein report the use of phenyl trimethylammonium iodide (PhMe(3)NI) as a safe, nontoxic, and easy-to-handle reagent for an absolutely monoselective N-methylation of amides and related compounds as well as for the N-methylation of indoles. In addition, we expanded the method to N-ethylation using PhEt(3)NI. The ease of operational setup, high yields of ≤99%, high functional group tolerance, and especially the excellent monoselectivity for amides make this method attractive for late-stage methylation of bioactive compounds.

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