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Issue 39, 2013
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A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

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Abstract

The development of multistep continuous flow reactions for the synthesis of important intermediates for the pharmaceutical industry is still a significant challenge. In the present contribution the biaryl-hydrazine unit of Atazanavir, an important HIV protease inhibitor, was prepared in a three-step continuous flow sequence in 74% overall yield. The synthesis involved Pd-catalyzed Suzuki–Miyaura cross-coupling, followed by hydrazone formation and a subsequent hydrogenation step, and additionally incorporates a liquid–liquid extraction step.

Graphical abstract: A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

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Article information


Submitted
16 Jul 2013
Accepted
12 Aug 2013
First published
14 Aug 2013

This article is Open Access

Org. Biomol. Chem., 2013,11, 6806-6813
Article type
Paper

A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

L. Dalla-Vechia, B. Reichart, T. Glasnov, L. S. M. Miranda, C. O. Kappe and R. O. M. A. de Souza, Org. Biomol. Chem., 2013, 11, 6806
DOI: 10.1039/C3OB41464G

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