The first radiosynthesis of 2-amino-5-[18F]fluoropyridines via a "minimalist" radiofluorination/palladium-catalyzed amination sequence from anisyl(2-bromopyridinyl)iodonium triflate. Issue 26 (20th June 2019)

• Record Type: Journal Article
• Authors: Pauton, Mathilde; Gillet, Raphaël; Aubert, Catherine; Bluet, Guillaume; Gruss-Leleu, Florence; Roy, Sébastien; Perrio, Cécile
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 26(2019)
• Page Start: 6359
• Page End: 6363
• Publication Date: 2019-06-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01187k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Radiofluorination of anisyl(2-bromopyridinyl)iodonium triflate under "minimalist" conditions: an entry to 2-amino-5-[ 18 F]fluoropyridines via Buchwald–Hartwig amination. Abstract : The synthesis of 2-amino-5-[ 18 F]fluoropyridines was achieved in 8–85% yields by palladium-catalyzed reaction of 2-bromo-5-[ 18 F]fluoropyridine with piperidine, dimethylamine, butylamine, methylpiperazine, benzylamine, aniline and 3-aminopyridine. 2-Bromo-5-[ 18 F]fluoropyridine was obtained by radiofluorination of anisyl(2-bromopyridinyl-5)iodonium triflate (88% yield). The radiofluorination step was performed under "minimalist" conditions to guarantee a successful subsequent amination reaction.