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An efficient and convergent synthesis of the potent and selective H3antagonist ABT-239

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
62
Issue
18
Identifiers
DOI: 10.1016/j.tet.2006.02.046
Keywords
  • H3Receptor Antagonist
  • Abt-239
  • Sonogashira Coupling
  • 2-(R)-Methylpyrrolidine

Abstract

Abstract An efficient and convergent process for the preparation of a potent and selective H 3 receptor antagonist, ABT-239, 1A was accomplished with an overall yield of 64%. The key step in the synthesis is a Sonogashira coupling/cyclization reaction of 1-but-3-ynyl-2-( R)-methylpyrrolidine ( 9 ) with 4′-hydroxy-3′-iodo-biphenyl-4-carbonitrile ( 3 ). Additionally, the key amine component 2-( R)-methylpyrrolidine ( 7 ) was effectively synthesized from the readily available Boc- l-prolinol with a simple catalytical hydrogenolysis as the key step. This column chromatography-free process is highlighted by several simple work-up and purification procedures and is amendable to the large-scale preparation of 1A .

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