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

ABSTRACT: We herein report the use of phenyl trimethylammonium iodide (PhMe₃NI) 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 PhEt₃NI. 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.

SUBMITTER: Templ J

PROVIDER: S-EPMC9578047 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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

Templ Johanna J Gjata Edma E Getzner Filippa F Schnürch Michael M

Organic letters 20221003 40

We herein report the use of phenyl trimethylammonium iodide (PhMe<sub>3</sub>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<sub>3</sub>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 f ...[more]

PMID: 36190781

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