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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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
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author Templ, Johanna
Gjata, Edma
Getzner, Filippa
Schnürch, Michael
author_facet Templ, Johanna
Gjata, Edma
Getzner, Filippa
Schnürch, Michael
author_sort Templ, Johanna
collection PubMed
description [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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spelling pubmed-95780472022-10-19 Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents Templ, Johanna Gjata, Edma Getzner, Filippa Schnürch, Michael Org Lett [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. American Chemical Society 2022-10-03 2022-10-14 /pmc/articles/PMC9578047/ /pubmed/36190781 http://dx.doi.org/10.1021/acs.orglett.2c02766 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Templ, Johanna
Gjata, Edma
Getzner, Filippa
Schnürch, Michael
Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title_full Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title_fullStr Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title_full_unstemmed Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title_short Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents
title_sort monoselective n-methylation of amides, indoles, and related structures using quaternary ammonium salts as solid methylating agents
url 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
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