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An efficient new method for the synthesis of 3‐[ 18 F]fluoro‐4‐aminopyridine via Yamada‐Curtius rearrangement
Author(s) -
Basuli Falguni,
Zhang Xiang,
Brugarolas Pedro,
Reich Daniel S.,
Swenson Rolf E.
Publication year - 2018
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.3560
Subject(s) - curtius rearrangement , chemistry , radioligand , yield (engineering) , 2 aminopyridine , positron emission tomography , pet imaging , chemical synthesis , derivative (finance) , radiochemistry , nuclear medicine , organic chemistry , biochemistry , receptor , medicine , materials science , economics , financial economics , metallurgy , in vitro
4‐Aminopyridine is a clinically approved drug to improve motor symptoms in multiple sclerosis. A fluorine‐18‐labeled derivative of this drug, 3‐[ 18 F]fluoro‐4‐aminopyridine, is currently under investigation for positron emission tomography (PET) imaging of demyelination. Herein, the Yamada‐Curtius reaction has been successfully applied for the preparation of this PET radioligand with a better radiochemical yield and improved specific activity. The overall radiochemical yield was 5 to 15% (n = 12, uncorrected) with a specific activity of 37 to 148 GBq/μmol (end of synthesis) in a 90 minute synthesis time. It is expected that this 1 pot Yamada‐Curtius reaction can be used to prepare similar fluorine‐18‐labeled amino substituted heterocycles.