Expedient Access to <sup>18</sup>F‐Fluoroheteroarenes via Deaminative Radiofluorination of Aniline‐Derived Pyridinium Salts-Reference-Cited by-同舟云学术

Expedient Access to ¹⁸F‐Fluoroheteroarenes via Deaminative Radiofluorination of Aniline‐Derived Pyridinium Salts

Published:2024-05-24 Issue:26 Volume:63 Page:
ISSN:1433-7851
Container-title:Angewandte Chemie International Edition
language:en
Short-container-title:Angew Chem Int Ed

Author:

Ford Joseph¹,Ortalli Sebastiano¹,Chen Zijun¹,Sap Jeroen B. I.¹²^ORCID,Tredwell Matthew³⁴^ORCID,Gouverneur Véronique¹^ORCID

Affiliation:

1. Department of Chemistry Chemistry Research Laboratory University of Oxford 12 Mansfield Road Oxford United Kingdom

2. Current address: Department of Translational Imaging Genentech Inc. 1 DNA Way South San Francisco, CA 94080 USA

3. Wales Research and Diagnostic PET Imaging Centre Cardiff University University Hospital of Wales Heath Park Cardiff CF14 4XN United Kingdom

4. School of Chemistry Cardiff University Main Building Park Place Cardiff CF10 3AT United Kingdom

Abstract

AbstractHerein, we disclose that pyridinium salts derived from abundant (hetero)anilines represent a novel precursor class for nucleophilic aromatic substitution reactions with [18F]fluoride. The value of this new 18F‐fluorodeamination is demonstrated with the synthesis of over 30 structurally diverse and complex heteroaryl 18F‐fluorides, several derived from scaffolds that were yet to be labelled with fluorine‐18. The protocol tolerates heteroarenes and functionalities commonly found in drug discovery libraries, and is amenable to scale‐up and automation on a commercial radiosynthesiser.

Funder

Engineering and Physical Sciences Research Council

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202404945

Reference83 articles.

1. Molecular Imaging with PET

3. Molecular imaging in drug development

4. Positron emission tomography molecular imaging for drug development

5. Strategies to facilitate the discovery of novel CNS PET ligands