A concise method for fully automated radiosyntheses of [18F]JNJ-46356479 and [18F]FITM via Cu-mediated 18F-fluorination of organoboranes

doi:10.1039/d0ra04943c

. 2020 Jul 2;10(42):25223-25227.

doi: 10.1039/d0ra04943c.

A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes

Gengyang Yuan¹, Timothy M Shoup¹, Sung-Hyun Moon¹, Anna-Liisa Brownell¹

Affiliations

Affiliation

¹ Gordon Center for Medical Imaging, Massachusetts General Hospital and Harvard Medical School, 3rd Avenue, Charlestown, MA 02129, USA. Email: gyyuan@mgh.harvard.edu; Email: abrownell@mgh.harvard.edu.

PMID: 33014351
PMCID: PMC7497470
DOI: 10.1039/d0ra04943c

Free PMC article

A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes

Gengyang Yuan et al. RSC Adv. 2020.

Free PMC article

. 2020 Jul 2;10(42):25223-25227.

doi: 10.1039/d0ra04943c.

Authors

Gengyang Yuan¹, Timothy M Shoup¹, Sung-Hyun Moon¹, Anna-Liisa Brownell¹

Affiliation

¹ Gordon Center for Medical Imaging, Massachusetts General Hospital and Harvard Medical School, 3rd Avenue, Charlestown, MA 02129, USA. Email: gyyuan@mgh.harvard.edu; Email: abrownell@mgh.harvard.edu.

PMID: 33014351
PMCID: PMC7497470
DOI: 10.1039/d0ra04943c

Abstract

A modified alcohol-enhanced ¹⁸F-fluorodeboronation has been developed for the radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM. Unlike the [¹⁸F]KF/K₂₂₂ approach, this method tolerates the presence of sensitive heterocycles in Bpin precursors 4 and 8 allowing a one-step ¹⁸F-fluorodeboronation on the fully automated TRACERlab™ FX_FN platform.

This journal is © The Royal Society of Chemistry 2020.

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Conflict of interest statement

There are no conflicts to declare.

Figures

**Fig. 1. Cu-mediated ¹⁸F-fluorination of organoboranes.**

**Scheme 1. Synthesis of JNJ-46356479 and its boronic pinacol ester precursor 4.**

**Scheme 2. Radiofluorination of [¹⁸F]JNJ-46356479.**

**Scheme 3. Cu-mediated ¹⁸F-fluorination of [¹⁸F]FTIM.**

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[1] Wang J. Sanchez-Rosello M. Acena J. L. del Pozo C. Sorochinsky A. E. Fustero S. Soloshonok V. A. Liu H. Chem. Rev. 2014;114:2432. doi: 10.1021/cr4002879. - DOI - PubMed

[2] Wang J. Sanchez-Rosello M. Acena J. L. del Pozo C. Sorochinsky A. E. Fustero S. Soloshonok V. A. Liu H. Chem. Rev. 2014;114:2432. doi: 10.1021/cr4002879. - DOI - PubMed

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[5] Shah P. Westwell A. D. J. Enzyme Inhib. Med. Chem. 2007;22:527. doi: 10.1080/14756360701425014. - DOI - PubMed

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[10] Phelps M. E. Proc. Natl. Acad. Sci. U. S. A. 2000;97:9226. doi: 10.1073/pnas.97.16.9226. - DOI - PMC - PubMed

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A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes

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A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes

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