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Synthesis 2008(6): 978-984  
DOI: 10.1055/s-2008-1032206
PAPER
© Georg Thieme Verlag Stuttgart · New York

Tetra- and Monoorganotin Reagents in Palladium-Mediated Cross-Coupling Reactions for the Labeling with Carbon-11 of PET Tracers

Thomas Bourdiera, Michael Huibana, Aline Huetb, Franck Sobrioa, Eric Fouquetb, Cécile Perrio*a, Louisa Barré*a
a Groupe de Développements Méthodologiques en Tomographie par Emission de Positons, UMR CEA 2E, Université de Caen-Basse Normandie, Centre Cyceron, 15 Boulevard Henri Becquerel, 14070 Caen Cedex, France
b Laboratoire de Chimie Organique et Organométallique, UMR CNRS 3802, Université Bordeaux I, 351 Cours de la Libération, 33405 Talence Cedex, France
Fax: +33(2)31470275; e-Mail: perrio@cyceron.fr; e-Mail: barre@cyceron.fr;
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Publication History

Received 28 November 2007
Publication Date:
28 February 2008 (online)

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Abstract

The palladium-catalyzed cross-coupling reactions between a (trimethylstannyl)arene and [11C]methyl iodide (Stille reaction) or between an aryl halide and a [11C]monomethyltin reagent issued from Lappert’s stannylene, were developed for the synthesis of polyfunctional [11C]methyl quinolines and quinolinimides as potential tracers for positron emission tomography (PET).

Key words

positron emission tomography - carbon-11 - Stille - monoorganotin­ - [11C]methyl iodide

    References

  • 1 Fowler JS. Wolf AP. Barrio JR. Mazziotta JC. Phelps ME. In Positron Emission Tomography and Autoradiography   Phelps ME. Mazziotta JC. Schelbert HR. Raven Press; New York: 1986.  Chap. 9-11.
    Google Scholar
  • 2 Långström B. Dannals RF. In Principles of Nuclear Medicine   Wagner HN. Szabo Z. Buchanan JW. W. B. Saunders W. B.; Philadelphia PA: 1995. 
    Google Scholar
  • 3a Fowler JS. Wolf AP. Acc. Chem. Res.  1997,  30:  181 
    CrossrefGoogle Scholar
  • 3b Ouari O. Polidori A. Pucci B. Tordo P. Chalier F. J. Org. Chem.  1999,  64:  3554 
    CrossrefGoogle Scholar
  • 4 Crouzel C. Långström B. Pike VW. Coenen HH. Appl. Radiat. Isot.  1987,  38:  601 
    CrossrefGoogle Scholar
  • 5 Buckman BO. VanBrocklin HF. Dence CS. Bergmann SR. Welch MJ. Katzenellenbogen JA. J. Med. Chem.  1994,  37:  2481 
    CrossrefGoogle Scholar
  • 6 Khilberg T. Långström B. Acta Chem. Scand.  1994,  48:  570 
    CrossrefGoogle Scholar
  • 7 Wüst F. Dence CS. McCarthy TJ. Welch MJ. J. Labelled Compd. Radiopharm.  2000,  43:  1289 
    CrossrefGoogle Scholar
  • 8 Hostetler ED. Fallis S. McCarthy TJ. Welch MJ. Katzenellenbogen JA. J. Org. Chem.  1998,  63:  1348 
    CrossrefGoogle Scholar
  • 9 Andersson Y. Cheng A. Långström B. Acta Chem. Scand.  1995,  49:  683 
    CrossrefGoogle Scholar
  • 10 Suzuki M. Doi H. Björkman M. Andersson Y. Långström B. Watanabe Y. Noyori R. Chem. Eur. J.  1997,  3:  2039 
    CrossrefGoogle Scholar
  • 11 Björkman M. Andersson Y. Doi H. Kato K. Suzuki M. Noyori R. Watanabe Y. Långström B. Acta Chem. Scand.  1998,  52:  635 
    CrossrefGoogle Scholar
  • 12 Björkman M. Doi H. Resul B. Suzuki M. Noyori R. Watanabe Y. Långström B. J. Labelled Compd. Radiopharm.  2000,  43:  1327 
    CrossrefGoogle Scholar
  • 13 Suzuki M. Doi H. Björkman M. Långström B. Watanabe Y. Noyori R. Tetrahedron  2000,  56:  8263 
    CrossrefGoogle Scholar
  • 14 Tarkiainen J. Vercouillie J. Emond P. Sandell J. Hiltunen J. Frangin Y. Guilloteau D. Halldin C. J. Labelled Compd. Radiopharm.  2001,  44:  1013 
    CrossrefGoogle Scholar
  • 15 Sandell J. Yu M. Emond P. Garreau L. Chalon S. Någren K. Guilloteau D. Halldin C. Bioorg. Med. Chem. Lett.  2002,  12:  3611 
    CrossrefGoogle Scholar
  • 16 Karimi F. Långström B. J. Labelled Compd. Radiopharm.  2002,  45:  423 
    CrossrefGoogle Scholar
  • 17 Madsen J. Merachtsaki P. Davoodpour P. Bergström M. Långström B. Andersen K. Thomsen C. Martiny L. Knudsen GM. Bioorg. Med. Chem.  2003,  11:  3447 
    CrossrefGoogle Scholar
  • 18 Langer O. Forngren T. Sandell J. Dollé F. Långström B. Någren K. Halldin C. J. Labelled Compd. Radiopharm.  2003,  46:  55 
    CrossrefGoogle Scholar
  • 19 Samuelsson L. Långström B. J. Labelled Compd. Radiopharm.  2003,  46:  263 
    CrossrefGoogle Scholar
  • 20 Antoni G. Khilberg T. Långström B. In Handbook of Radiopharmaceuticals, Radiochemistry and Applications   Welch MJ. Redvanly CS. Wiley; Chichester: 2003.  p.141-194  
    Google Scholar
  • 21 Huiban M. Huet A. Barré L. Sobrio F. Fouquet E. Perrio C. Chem. Commun.  2006,  97 
    CrossrefGoogle Scholar
  • 22 Harris DH. Lappert MF. J. Chem. Soc., Chem. Commun.  1974,  895 
    CrossrefGoogle Scholar
  • 23 Schaeffer CD. Zuckerman JJ. J. Am. Chem. Soc.  1974,  96:  7160 
    CrossrefGoogle Scholar
  • 24 Giardina GAM. Sarau HM. Farina C. Medhurst AD. Grugni M. Foley JJ. Raveglia LF. Schmidt DB. Rigolio R. Vassallo M. Vecchietti V. Hay DWP. J. Med. Chem.  1996,  39:  2281 
    CrossrefGoogle Scholar
  • 25 Giardina GAM. Raveglia LF. Grugni M. Sarau HM. Farina C. Medhurst AD. Graziani D. Schmidt DB. Rigolio R. Luttmann M. Cavagnera S. Foley JJ. Vecchietti V. Hay DWP. J. Med. Chem.  1999,  42:  1053 
    CrossrefGoogle Scholar
  • 26 Sarau HM. Griswold DE. Potts B. Bush W. Sandhu P. Lundberg D. Foley JJ. Schmidt DB. Webb EF. Martin LD. Legos JJ. Whitmore RG. Barone FC. Medhurst AD. Luttmann MA. Giardina GAM. Hay DWP. J. Pharmacol. Exp. Ther.  2000,  295:  373 
    Google Scholar
  • 27 Langlois X. Te Riele P. Wintmolders C. Leysen JE. Jurzak M. J. Pharmacol. Exp. Ther.  2001,  299:  712 
    Google Scholar
  • 28 Bennacef I. Perrio C. Lasne M.-C. Barré L. J. Org. Chem.  2007,  72:  2161 
    CrossrefGoogle Scholar
  • 29 Quinolines 3 and 4 were original compounds synthesized in our laboratory. Their affinities towards NK-3 receptors were identical to that of SB 222200. For in vitro evaluation experimental procedure, see: Bennacef I. Tymciu S. Dhilly M. Mongin F. Quéguiner G. Lasne M.-C. Barré L. Perrio C. J. Org. Chem.  2004,  69:  2622 
    CrossrefGoogle Scholar
  • 30 Barn DR. Caulfield WL. Cottney J. McGurk K. Morphy JR. Rankovic Z. Roberts B. Bioorg. Med. Chem.  2001,  9:  2609 
    CrossrefGoogle Scholar
  • 31 Bourdier T. Poisnel G. Dhilly M. Delamare J. Henry J. Debruyne D. Barré L. Bioconjugate Chem.  2007,  18:  538 
    CrossrefGoogle Scholar
  • 32 Hervé A. Rodriguez AL. Fouquet E. J. Org. Chem.  2005,  70:  1953 
    CrossrefGoogle Scholar
  • 33 Bennacef I. Tymciu S. Dhilly M. Lasne M.-C. Debruyne D. Perrio C. Barré L. Bioorg. Med. Chem.  2004,  12:  4533 
    CrossrefGoogle Scholar