A method for synthesizing aryl F-18 labeled sulfonyl chlorides and its application in labeling amine compounds

Aryl F-18 labeled sulfonyl chlorides were prepared by photocatalytic fluorination and oxidative chlorination reactions, which solved the problem of insufficient synthesis methods in the existing technology. This method achieved efficient preparation of aryl F-18 labeled sulfonyl chlorides and high conversion rate labeling of amine compounds, and is suitable for the development of various PET probes.

CN122036563BActive Publication Date: 2026-08-04SICHUAN UNIV
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Patent Information

Application Number
CN202610507860.7
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2026-04-17
Publication Date
2026-08-04
Estimated Expiration
2046-04-17

AI Technical Summary

Technical Problem

The lack of efficient methods for synthesizing aryl F-18 labeled sulfonyl chlorides in the existing technology limits their application in PET probe preparation and development.

Method used

Using thiophenol derivatives as labeling precursors, aryl F-18 labeled sulfonyl chlorides were prepared via photocatalytic fluorination and oxidative chlorination. These chlorides served as highly active intermediates for sulfonation reactions with amine compounds under mild conditions.

Benefits of technology

The efficient synthesis of aryl F-18 labeled sulfonyl chlorides was achieved with a radiochemical conversion rate of 92-95% and a conversion rate of up to 98% with sulfonation reactions with amine compounds. In particular, the labeling rate in the synthesis of AMPA receptor PET imaging agent [18F]2 was much higher than that of existing methods, and the conditions were milder.

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Abstract

The application belongs to the technical field of biological medicine, and discloses a synthesis method of aryl F-18 labeled sulfuryl chloride and application of the aryl F-18 labeled sulfuryl chloride in amine compound labeling. The method takes thiophenol derivative as a labeling precursor, obtains F-18 labeled thiophenol intermediate through photocatalytic aryl F-18 fluorination reaction, and then obtains aryl F-18 labeled sulfuryl chloride through N-chlorosuccinimide oxidation chlorination. The obtained aryl F-18 labeled sulfuryl chloride (4-[ 18 F] fluorobenzenesulfonyl chloride) can occur sulfurylization reaction with various amine compounds at room temperature, and the radiochemical conversion rate is as high as 98%. The application is successfully applied to novel synthesis of AMPA receptor PET imaging agent[ 18 F]2 (the conversion rate is 96%, which is much higher than 13% reported in the literature). The application has the advantages of mild reaction condition, high conversion rate and wide substrate application range, and provides an efficient method for innovative preparation of F-18 labeled PET probes.
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