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

Analytical Data and Compound Numbering (in paper numbering vs. ELN entries) for the Publication entitled:"Monoselective N-Methylation of Amides, Indoles, and Related Structures Using Quaternary Ammonium Salts as Solid Methylating Agents"

The paper was published on 2022-10-03 in Organic Letters

Org. Lett. 2022, 24, 40, 7315-7319

DOI: 10.1021/acs.orglett.2c02766

Authors: Johanna Templ, Edma Gjata, Filippa Getzner, and Michael Schnürch

Funded by the Austrian Science Fund (FWF, project number P33064-N)

Context and methodology

In this Publication, we 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.

The publication and its Supporting Information can be found as open-access files on the publisher's website (see DOI above).

All detailed files containing the analytical raw data, for all compounds given in the Supporting Information of the manuscript are uploaded. An additional PDF file named Org. Lett. 2022, 24, 40, 7315-7319_compound number list.pdf is uploaded, that should clearly link the compound number given in the paper to the respective entry in the ELN (jotempl) and the respective analytical data files. 

Technical details

The files uploaded contain the FIDs of NMR spectra recorded by an in-house Bruker Spectrometer. A software to display NMR-spectra is needed, such as MestreNova or Topspin).

HRMS data is uploaded too and has to be processed via MassHunter software.