Synthesis of amide derivatives for electron deficient amines and functionalized carboxylic acids using EDC and DMAP and a catalytic amount of HOBt as the coupling reagents

Arun K Ghosh; Dana Shahabi

doi:10.1016/j.tetlet.2020.152719

Synthesis of amide derivatives for electron deficient amines and functionalized carboxylic acids using EDC and DMAP and a catalytic amount of HOBt as the coupling reagents

Tetrahedron Lett. 2021 Jan 19:63:152719. doi: 10.1016/j.tetlet.2020.152719. Epub 2020 Dec 25.

Authors

Arun K Ghosh¹, Dana Shahabi¹

Affiliation

¹ Department of Chemistry, Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, United States.

Abstract

A convenient protocol for amide bond formation for electron deficient amines and carboxylic acids is described. Amide coupling of aniline derivatives has been investigated with a number of reagents under a variety of reaction conditions. The use of 1 equivalent of EDC and 1 equivalent of DMAP, catalytic amount of HOBt and DIPEA provided the best results. This method is amenable to the synthesis of a range of functionalized amide derivatives with electron deficient and unreactive amines.

Keywords: Amidation; Amines; Carboxylic acids; DMAP; EDC; HOBt.

Abstract

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