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Synthesis of bipyridine analogues of metomidate for conjugate formation with the 99mTc(I)-tricarbonyl complex

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Abstract

Ethyl 2,2′-bipyridine-5-carboxylate was converted to (2,2′-bipyridine-5-yl)methanol and (S)-1-(2,2′-bipyridine-5-yl)ethanol. The latter synthesis comprised five steps and resolution by HPLC on a chiral stationary phase. Both alcohols were reacted with methyl 1H-imidazole-5-carboxylate in a Mitsunobu reaction to give mixtures of the desired methyl 1-(2,2′-bipyridine-5-yl)alkyl-1H-imidazole-5-carboxylate as main product and the methyl 1-(2,2′-bipyridine-5-yl)alkyl-1H-imidazole-4-carboxylate as side product. The structure of (R)-(−)-methyl 1-(2,2′-bipyridine-5-yl)ethyl-1H-imidazole-4-carboxylate was determined by X-ray structure analysis.

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Acknowledgments

The project was supported by the Austrian National Bank (Jubiläumsfonds Project No. 8680). We thank S. Felsinger for recording the NMR spectra and Dr M. Berger for proofreading the manuscript.

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Vienna, Vienna, Austria

    Anna Schweifer, Frank Wuggenig & Friedrich Hammerschmidt

  2. Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, 1060, Vienna, Austria

    Kurt Mereiter

Authors
  1. Anna Schweifer
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  2. Ilse Zolle
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  3. Frank Wuggenig
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  4. Kurt Mereiter
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  5. Friedrich Hammerschmidt
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Corresponding author

Correspondence to Friedrich Hammerschmidt.

Additional information

Ilse Zolle: deceased April 8 2009.

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Schweifer, A., Zolle, I., Wuggenig, F. et al. Synthesis of bipyridine analogues of metomidate for conjugate formation with the 99mTc(I)-tricarbonyl complex. Monatsh Chem 141, 437–443 (2010). https://doi.org/10.1007/s00706-010-0278-4

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  • DOI: https://doi.org/10.1007/s00706-010-0278-4

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