2-chlorophenyl zinc bromide: a convenient nucleophile for the mannich-related multicomponent synthesis of clopidogrel and ticlopidine

Molecules. 2010 Nov 11;15(11):8144-55. doi: 10.3390/molecules15118144.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides / chemistry*
  • Clopidogrel
  • Cobalt / chemistry
  • Molecular Structure
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / chemistry
  • Ticlopidine / analogs & derivatives*
  • Ticlopidine / chemical synthesis*
  • Ticlopidine / chemistry*
  • Zinc / chemistry
  • Zinc Compounds / chemistry*

Substances

  • Bromides
  • Platelet Aggregation Inhibitors
  • Zinc Compounds
  • Cobalt
  • Clopidogrel
  • Zinc
  • Ticlopidine
  • zinc bromide