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

Isabelle Aillaud, Caroline Haurena, Erwan Le Gall, Thierry Martens, Gino Ricci

Molecules. 2010 Nov 11;15(11):8144-55.

PMID: 21072025

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).

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7699458 Zinc bromide Zinc bromide 7699-45-8 Price
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