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Synthesis 2023; 55(14): 2186-2194
DOI: 10.1055/a-2035-0040
paper

A New Method for the Synthesis of 1-Methyl-1H-indole-3-carboxylate Derivatives, Employing Copper(II)

Ali Akbari  ∗
,
Muhammad Saleh Faryabi
We are grateful for the financial support provided by the University of Jiroft for this research, which leads to our exceptional success.
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Abstract

We report an efficient method for synthesizing 1-methyl-1H-indole-3-carboxylates by cross-dehydrogenative coupling. However, the coupling reactions are a way to functionalize the α-carbon of iminiums from tertiary amines. The synthesis of 1-methyl-1H-indole-3-carboxylates from N,N-dimethylaniline with bromoacetates has not been reported. In the present work, we describe a novel route for synthesizing 1-methyl-1H-indole-3-carboxylates with N,N-dimethylaniline and a wide range of phenyl bromoacetate derivatives. Features such as a simple procedure and good to excellent yields (69–90%) make this method a highly efficient procedure for the preparation of indole derivatives using Cu(OAc)2·H2O as a catalyst in the presence of tert-butyl hydroperoxide.

Key words

1-methyl-1H-indole-3-carboxylates - heterocycles - cross-dehydrogenative coupling - copper - heterogeneous catalysis - oxidation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2035-0040.
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Publication History

Received: 08 December 2022

Accepted after revision: 14 February 2023

Accepted Manuscript online:
14 February 2023

Article published online:
29 March 2023

© 2023. Thieme. All rights reserved

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