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Development, Optimization, and Scope of the Radiosynthesis of 3/5-[ 18 F]Fluoropyridines from Readily Prepared Aryl(pyridinyl) Iodonium Salts: The Importance of TEMPO and K 2 CO 3

Abstract : A robust process for the radiosynthesis of 3/5-[18F]fluoropyridines has been developed by radiofluorination of iodonium triflates using K18F/K2CO3/K222 complex in the presence of TEMPO. Both electronically deficient and enriched iodonium salts were readily obtained from the corresponding 3/5-iodopyridines and afforded the corresponding 3/5-[18F]fluoropyridines in 6–78% yields. The concentrations of K2CO3 and TEMPO were found to be crucial for the radiofluorination efficiency. The process was validated using two automated systems for the 18F-radiolabeling of 2-chloro and 2-carboxamido-5-fluoropyridines carried out in 10–20% yields.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02110378
Contributor : Carole Brunaud <>
Submitted on : Thursday, April 25, 2019 - 1:25:13 PM
Last modification on : Thursday, October 1, 2020 - 4:13:02 PM

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Mathilde Pauton, Catherine Aubert, Guillaume Bluet, Florence Gruss-Leleu, Sébastien Roy, et al.. Development, Optimization, and Scope of the Radiosynthesis of 3/5-[ 18 F]Fluoropyridines from Readily Prepared Aryl(pyridinyl) Iodonium Salts: The Importance of TEMPO and K 2 CO 3. Organic Process Research and Development, American Chemical Society, 2019, 23 (5), pp.900-911. ⟨10.1021/acs.oprd.9b00021⟩. ⟨hal-02110378⟩

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