A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging
Hoover, Andrew J.
Narayanam, Maruthi Kumar
Murphy, Jennifer M.
van Dam, R. Michael
MetadataShow full item record
CitationHoover, Andrew J., Mark Lazari, Hong Ren, Maruthi Kumar Narayanam, Jennifer M. Murphy, R. Michael van Dam, Jacob M. Hooker, and Tobias Ritter. 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. http://dx.doi.org/10.1021/acs.organomet.6b00059.
AbstractTranslation of new 18F-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 18F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful 18F-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 [18F]fluoride of human doses of [18F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [18F]5-fluorouracil precursor. Routine production of >10 mCi doses of [18F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [18F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated 18F-fluorination.
Citable link to this pagehttp://nrs.harvard.edu/urn-3:HUL.InstRepos:26860130