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Rapid and Efficient Synthesis of 11 C‐Labeled Benzimidazolones Using [ 11 C]Carbon Dioxide
Author(s) -
Horkka Kaisa,
Dahl Kenneth,
Bergare Jonas,
Elmore Charles S.,
Halldin Christer,
Schou Magnus
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803561
Subject(s) - synthon , chemistry , carbon dioxide , reagent , ligand (biochemistry) , radiochemistry , carbon 14 , nuclear chemistry , stereochemistry , organic chemistry , physics , receptor , biochemistry , quantum mechanics
[ 11 C]Carbon dioxide is an attractive synthon for the labeling of positron emission tomography (PET) tracers for subsequent use in biomedical research and drug development. In this study, [ 11 C]CO 2 was used for direct 11 C‐labeling of a set of cyclic aromatic ureas starting from their corresponding ortho ‐phenylenediamines, BEMP (2‐ tert ‐butylimino‐2‐diethylamino‐1,3‐dimethylperhydro‐1,3,2‐diazaphosphorine) as fixation base, and Mitsunobu reagents (DBAD, n Bu 3 P) for the intramolecular cyclization. The procedure is rapid (6 minutes total synthesis time), mild (proceeds at room temperature) and provided a set of 11 C‐benzimidazolones in good to excellent radiochemical yields. As a final testament to the utility of this method, the beta‐adrenoceptor PET ligand [ 11 C]CGP12177, was successfully prepared using the optimized conditions.