Potassium tert-Butoxide Facilitated Amination of Carboxylic Acids with N,N-Dimethylformamide

Abstract

Herein a practical and efficient potassium tert-butoxide (KO ^t Bu)-facilitated amination of carboxylic acids with N,N-dimethylamine is described. In the presence of catalytic amount of KO ^t Bu, a variety of aliphatic and aromatic carboxylic acids are transformed to N,N-dimethylamides using DMF as the dimethylamine reagent with the assistance of trimethylacetic anhydride. The applicability of this protocol is demonstrated by late-stage dimethylamidation of complex drug molecules. A plausible reaction mechanism involving KO ^t Bu-facilitated in situ amine generation from formamide decomposition and anhydride-mediated condensation is proposed on the basis of mechanistic investigations.

Key words

amidation - N,N-dimethylformamide - carboxylic acid - potassium­ tert-butoxide

Publikationsverlauf

Eingereicht: 05. März 2022

Angenommen nach Revision: 03. April 2022

Accepted Manuscript online:
05. April 2022

Artikel online veröffentlicht:
17. Mai 2022

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