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

Index: Molecules 15(11) , 8144-55, (2010)

Full Text: HTML

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).