Templ, J., Gjata, E., Getzner, F., & Schnürch, M. (2022). Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents. Organic Letters, 24(40), 7315–7319. https://doi.org/10.1021/acs.orglett.2c02766
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.
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Forschungsinfrastruktur:
Zentrum für Kernspinresonanzspektroskopie
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Projekttitel:
Substitution von gasförmigen Reagenzien durch Feststoffe: P 33064-N (Fonds zur Förderung der wissenschaftlichen Forschung (FWF))
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