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Molecules 2010, 15(11), 8144-8155; https://doi.org/10.3390/molecules15118144

2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine

1
Électrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris Est, ICMPE, UMR 7182 CNRS - Université Paris-Est Créteil Val-de-Marne, 2-8 rue Henri Dunant, 94320 Thiais, France
2
Sanofi-Aventis, Process Development, 45 Chemin de Mételine, BP 15, 04201 Sisteron cedex, France
*
Author to whom correspondence should be addressed.
Received: 8 October 2010 / Revised: 2 November 2010 / Accepted: 9 November 2010 / Published: 11 November 2010
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Abstract

A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9).
Keywords: multicomponent reactions; organozinc reagents; amino acids; cobalt; zinc multicomponent reactions; organozinc reagents; amino acids; cobalt; zinc
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Aillaud, I.; Haurena, C.; Gall, E.L.; Martens, T.; Ricci, G. 2-Chlorophenyl Zinc Bromide: A Convenient Nucleophile for the Mannich-Related Multicomponent Synthesis of Clopidogrel and Ticlopidine. Molecules 2010, 15, 8144-8155.

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