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Isotopologues of potassium 2,2,2-trifluoroethoxide for applications in positron emission tomography and beyond

Author

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  • Qunchao Zhao

    (National Institutes of Health)

  • Sanjay Telu

    (National Institutes of Health)

  • Susovan Jana

    (National Institutes of Health)

  • Cheryl L. Morse

    (National Institutes of Health)

  • Victor W. Pike

    (National Institutes of Health)

Abstract

The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF3CH2OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t1/2 = 20.4 min) or fluorine-18 (t1/2 = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11C- or 18F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.

Suggested Citation

  • Qunchao Zhao & Sanjay Telu & Susovan Jana & Cheryl L. Morse & Victor W. Pike, 2024. "Isotopologues of potassium 2,2,2-trifluoroethoxide for applications in positron emission tomography and beyond," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49975-7
    DOI: 10.1038/s41467-024-49975-7
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