Synthesis of (18)F-Arenes from Spirocyclic Iodonium(III) Ylides via Continuous-Flow Microfluidics.

ABSTRACT: Spirocyclic hypervalent iodine(III) ylides have proven to be synthetically versatile precursors for efficient radiolabelling of a diverse range of non-activated (hetero)arenes, highly functionalised small molecules, building blocks and radiopharmaceuticals from [(18)F]fluoride ion. Herein, we report the implementation of these reactions onto a continuous-flow microfluidic platform, thereby offering an alterative and automated synthetic procedure of a radiopharmaceutical, 3-[(18)F]fluoro-5-[(pyridin-3-yl)ethynyl]benzonitrile ([(18)F]FPEB) and a routinely used building block for click-radiochemistry, 4-[(18)F]fluorobenzyl azide. This new protocol was applied to the synthesis of [(18)F]FPEB (radiochemical conversion (RCC) = 68 ± 5%) and 4-[(18)F]fluorobenzyl azide (RCC=68 ± 5%; isolated radiochemical yield = 24±0%). We anticipate that the high throughput microfluidic platform will accelerate the discovery and applications of (18)F-labelled building blocks and labelled compounds prepared by iodonium ylide precursors as well as the production of radiotracers for preclinical imaging studies.

SUBMITTER: Calderwood S 

PROVIDER: S-EPMC4976495 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature