Skip to main content
SpringerLink
Log in

Radiofluorination of 2-fluoropyridines by isotopic exchange with [18F]fluoride

  • Published:
Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

In homoaromatic systems, isotopic exchange (18F/19F) was previously (J Label Compd Radiopharm 18(12):1721–1730 [2], J Chem Soc Perkin Trans 1(3):295–298 [3]) proven to be advantageous, yet in general specific activity is thought to be low. For heteroaromatic systems, in particular, very few examples are published regarding the 18F-labelling of 2-substituted pyridines (J Label Compd Radiopharm 42:975–985 [9]). Therefore, in 2-fluoropyridines, we decided to study the 18F labelling by isotopic exchange (18F/19F). The radiochemical yield for 2-fluoropyridine was 90 ± 2%. Even if 2-fluoropyridine was substituted by an electron-donating group such as a methyl or a methoxy group, radiochemical yields were 80 ± 1 and 78 ± 1%, respectively. Although in benzenes, these substituents are known to decrease nucleophilic substitutions by 18F-Fluoride significantly. Moreover, by choosing appropriate concentrations of 2-fluoropyridines, reasonably high specific activities up to 10 GBq/μmol were obtained.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Dollé F (2005) Curr Pharm Des 11:3221–3235

    Article  Google Scholar 

  2. Cacace F, Speranza M, Wolf AP, Fowler JS (1981) J Label Compd Radiopharm 18(12):1721–1730

    Article  CAS  Google Scholar 

  3. de Oliveira Baptista MJV, Widdowson DA (1978) J Chem Soc Perkin Trans 1(3):295–298

    Article  Google Scholar 

  4. Shen B, Löffler D, Zeller KP, Ubele M, Reischl G, Machulla HJ (2007) J Appl Radiat Isot 65(11):1227–1231

    Article  CAS  Google Scholar 

  5. Shen B, Löffler D, Ubele M, Reischl G, Zeller KP, Machulla HJ (2007) J Nucl Med 48(Suppl 2):317p

    Google Scholar 

  6. Shen B, Löffler D, Reischl G, Machulla HJ, Zeller KP (2009) J Fluor Chem 130(2):216–224

    Article  CAS  Google Scholar 

  7. Irie T, Fukushi K, Ido T (1982) J Appl Radiat Isot 33:445–448

    Article  CAS  Google Scholar 

  8. Knust EJ, Müller-Platz C, Schüller M (1982) J Radioanal Chem 74:283–291

    Article  CAS  Google Scholar 

  9. Dolci L, Dollé F, Jubeau S, Vaufrey F, Crouzel C (1999) J Label Compd Radiopharm 42:975–985

    Article  CAS  Google Scholar 

  10. Malik N, Solbach C, Voelter W, Machulla HJ (2010) J Radioanal Nucl Chem 283:757–764

    Article  CAS  Google Scholar 

  11. Shen B (2008) Studies on the nucleophilic aromatic 18F-fluorination-from model compounds to aromatic amino acids. Dissertation. http://tobias-lib.ub.uni-tuebingen.de/volltexte/2008/3666/pdf/doktorarbeit_final_081219.pdf

  12. Ding YS, Shiue CY, Fowler JS, Wolf AP, Plenevaux A (1990) J Fluor Chem 48:189–205

    Article  CAS  Google Scholar 

  13. Rengan R, Chakraborty PK, Kilbourn MR (1993) J Label Compd Radiopharm 33(7):563–572

    Article  CAS  Google Scholar 

  14. Breitmaier E, Voelter W (1987) Carbon-13 nmr spectroscopy—high resolution methods and applications in organic chemistry and biochemistry, vol 135. VCH Verlanggesellschaft GmbH, D-6940 Weinheim, Germany, pp 184–185. ISBN: 3-527-26466-3

Download references

Acknowledgment

The project was supported by a research grant (no. MA 1096/8-1) of Deutsche Forschungsgemeinschaft (DFG) and by DAAD awarded scholarship. Moreover, the authors are particularly grateful to Prof. Dr. S. N. Reske for allowing to continue and finish the project while giving continuous encouragement and stimulation throughout this project.

Author information

Authors and Affiliations

  1. Klinik für Nuklearmedizin, Universitätsklinikum, Universität Ulm, Albert-Einstein-Allee 23, D-89081, Ulm, Germany

    Noeen Malik & Christoph Solbach

  2. Department of Radiopharmacy, Eberhard-Karls-University, Tübingen, Germany

    Hans-Jürgen Machulla

  3. Interfacultary Institute for Biochemistry, Eberhard-Karls-University, Tübingen, Germany

    Wolfgang Voelter

Authors
  1. Noeen Malik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wolfgang Voelter
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hans-Jürgen Machulla
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Christoph Solbach
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Noeen Malik.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Malik, N., Voelter, W., Machulla, HJ. et al. Radiofluorination of 2-fluoropyridines by isotopic exchange with [18F]fluoride. J Radioanal Nucl Chem 287, 287–292 (2011). https://doi.org/10.1007/s10967-010-0678-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10967-010-0678-2

Keywords

Search

Navigation