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. 2010 Feb 5;12(3):412-5.
doi: 10.1021/ol902433a.

Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles

Ananda Herath  1 , Russell Dahl, Nicholas D P Cosford
Affiliations

Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles

Ananda Herath et al. Org Lett. .

Abstract

The first continuous flow synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids directly from 2-aminopyridines and bromopyruvic acid has been developed, representing a significant advance over the corresponding in-flask method. The process was applied to the multistep synthesis of imidazo[1,2-a]pyridine-2-carboxamides, including a Mur ligase inhibitor, using a two microreactor, multistep continuous flow process without isolation of intermediates.

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Figures

Figure 1
Figure 1
Continuous flow sequence for the synthesis of imidazo[1,2-a]pyridine-2-carboxamides.
Scheme 1
Scheme 1
In-flask preparation of imidazo[1,2-a]pyridine-2-carboxylic acids and imidazo[1,2-a]pyridine-2-carboxamides.
Scheme 2
Scheme 2
Continuous flow preparation of Mur ligase inhibitor 3.
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