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2‐Bromo‐6‐[ 18 F]fluoropyridine: two‐step fluorine‐18 radiolabelling via transition metal‐mediated chemistry
Author(s) -
Betts Helen M.,
Robins Edward G.
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3147
Subject(s) - synthon , chemistry , fluorine , nucleophile , fluoride , transition metal , molecule , yield (engineering) , combinatorial chemistry , organic chemistry , inorganic chemistry , catalysis , materials science , metallurgy
Novel radiolabelling methods are important for the development of new tracers for positron emission tomography. Direct nucleophilic fluorination of aromatic rings with [ 18 F]fluoride is limited to activated substrates, restricting the application of this approach. Inspired by transition metal‐mediated transformations, a fluorine‐18 synthon was prepared to supplement the radiolabelling methods available for molecules unsuitable for direct labelling. 2‐Bromo‐6‐[ 18 F]fluoropyridine (denoted [ 18 F]1) was prepared in high yield, and palladium‐mediated cross‐coupling reactions were exemplified. High incorporation of fluoride and efficient cross‐coupling reactions demonstrate that compound [ 18 F]1 holds promise as a new synthon for construction of fluorine‐18‐labelled molecules via transition metal‐mediated reactions.