No-carrier added synthesis of 18F-labelled nucleosides using Stille cross-coupling reactions with 4-[18F]fluoroiodobenzene

✍ Scribed by Frank R. Wüst; Torsten Kniess

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: French
• Weight: 137 KB
• Volume: 47
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.834

✦ Synopsis

Abstract

The radiosyntheses of 5‐(4′‐[^18^F]fluorophenyl)‐uridine [^18^F]‐11 and 5‐(4′‐[^18^F]fluorophenyl)‐2′‐deoxy‐uridine [^18^F]‐12 are described. The 5‐(4′‐[^18^F]fluoro‐phenyl)‐substituted nucleosides were prepared via a Stille cross‐coupling reaction with 4‐[^18^F]fluoroiodobenzene followed by basic hydrolysis using 1 M potassium hy‐droxide. The Stille cross‐coupling reaction was optimized by screening various palladium complexes, additives and solvents. By using optimized labelling conditions (Pd~2~(dba)~3~/CuI/AsPh~3~ in DMF/dioxane (1:1), 20 min at 65°C), 550 MBq of [4‐^18^F]fluoroiodobenzene could be converted into 120 MBq (33%, decay‐corrected) of 5‐(4′‐[^18^F]fluorophenyl)‐2′‐deoxy‐uridine [^18^F]‐12 within 40 min, including HPLC purification. Copyright © 2004 John Wiley & Sons, Ltd.