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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 4
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Original Articles

Facile synthesis of TEG-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine and PET imaging agent [F]florbetapir ([F]AV-45)

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Pages 422-427 | Received 11 Aug 2017, Published online: 18 Jan 2018

References

  • (a) Wong, D.; Rosenberg, P.; Zhou, Y.; Kumar, A.; Raymont, V.; Ravert, H.; Dannals, R.; Nandi, A.; Brasic, J.; Ye, W.; J. Nucl. Med. 2010, 51, 913–920; (b) Kung, H.; Choi, S.; Qu, W.; Zhang, W.; Skovronsky, D. J. Med. Chem. 2009, 53, 933–941; (c) Choi, S.; Golding, G.; Zhuang, Z.; Zhang, W.; Lim, N.; Hefti, F.; Benedum, T.; Kilbourn, M.; Skovronsky, D.; Kung, H. J. Nucl. Med. 2009, 50, 1887–1894; (d) Zhang, W.; Kung, M.; Oya, S.; Hou, C.; Kung, H. Nucl. Med. Biol. 2007, 34, 89–97; (e) Clark, C. M.; Schneider, J. A.; Bedell, B. J.; Beach, T. G.; Bilker, W. B.; Mintun, M. A.; Pontecorvo, M. J.; Hefti, F.; Carpenter, A. P.; Flitter, M. L.; J. Am. Med. Assoc. 2011, 305, 275–283; (f) Kung, M.-P.; Kung, H. F. WO Patent 2007/126733 A2, 2007.
  • Zha, Z.; Choi, S. R.; Ploessl, K.; Lieberman, B. P.; Qu, W.; Hefti, F.; Mintun, M.; Skovronsky, D.; Kung, H. F. J. Med. Chem. 2011, 54, 8085–8098.
  • For synthesis of AV-45 from TEG-substituted 4-(N-methyl-N-Boc-amino)styrylpyridine (5), please see: (a) Hayashi, K.; Tachibana, A.; Tazawa, S.; Mizukawa, Y.; Osaki, K.; Morimoto, Y.; Zochi, R.; Kurahashi, M.; Aki, H.; Takahashi, K. J. Labelled Compd. Radiopharm. 2013, 56, 295–300. For other methods for synthesis of AV-45, please see: 1f and (b) Benedum, T.; Golding, G.; Lim, N.; Zhang, W. US Patent 2010/172836 A1, 2010; (c) Lee, S. J.; Oh, S. J.; Moon, D. H.; Ryu, J. S.; Kim, J. S.; Lee, J. J. EP Patent 2810926 A1, 2014; (d) Piramal, I. S. A; Berndt, M.; Friebe, M.; Samson, F.; Braun, R.; Garke, G.; Patt, M.; Schiddan, A.; Smuda, C. JP Patent 2016/47831 A1, 2016.
  • Li, Z.; Liu, B.; Duan, W.; Zhu, L. Syn. Commun. 2015, 45, 2740–2747.
  • For some reviews, see: (a) Maercker, A. Org. React. 1965, 14, 270–490 (b) Carruthers, W. Some Modern Methods of Organic Synthesis; Cambridge University Press: Cambridge, UK, 1971; pp 81–90; (c) Hoffmann, R. W. Angew. Chem. Int. Ed. 2001, 40, 1411–1416.
  • Abu, T. K.; Lokman, H. C.; Subrata, G. Tetrahedron Lett. 2004, 45, 7891–7894.

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