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A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging

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Citation

Hoover, A. J., Lazari, M., Ren, H., Narayanam, M. K., Murphy, J. M., van Dam, R. M., et al. (2016). A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging. Organometallics, 35(7), 1008-1014. doi:10.1021/acs.organomet.6b00059.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-617A-E
Abstract
Translation of new F-18-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for F-18-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful F-18-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [F-18]fluoride of human doses of [F-18]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel 6-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [F-18]5-fluorouracil precursor. Routine production of >10 mCi doses of [F-18]5-fluorouracil was accomplished with a new instrument for azeotrope-free [F-18]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated F-18-fluorination.