Molecules (Nov 2010)

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

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

DOI
https://doi.org/10.3390/molecules15118144
Journal volume & issue
Vol. 15, no. 11
pp. 8144 – 8155

Abstract

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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).

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