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Synthesis 2009(12): 1979-1982  
DOI: 10.1055/s-0029-1216787
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Short and Efficient Synthesis of 3-{2-[2-(Bromomethyl)thiazol-4-yl]-ethynyl}-5-fluorobenzonitrile: A Precursor for PET Radioligand [18F]SP203

Madathil B. Gopinathan, Chunyang Jin, Kenneth S. Rehder*
Center for Organic and Medicinal Chemistry, RTI International, Research Triangle Park, NC 27709, USA
Fax: +1(919)5418868; e-Mail: krehder@rti.org;
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Publication History

Received 8 January 2009
Publication Date:
30 April 2009 (online)

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Abstract

An improved synthesis of 3-{2-[2-(bromomethyl)thia­zol-4-yl]ethynyl}-5-fluorobenzonitrile, a precursor for PET radioligand [¹8F]SP203, is described, wherein a new synthon was employed for Sonogashira coupling with 3-bromo-5-fluorobenzonitrile. The new five-step synthesis provided the title compound in 56% overall yield starting from 4-bromo-2-formylthiazole.

Key words

PET ligand - fluorine - Sonogashira coupling - palladium - bromination