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Synthesis of 5-(sulfamoylmethyl)indoles by mild Negishi coupling and their application in almotriptan

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Abstract

A new synthetic route of almotriptan was described. The application of Negishi coupling reaction simplified the process and significantly improved the yield. The synthetic route was also expected to be general for the synthesis of other tryptamines like sumatriptan and avitriptan.

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References

  1. Leonardi M., Steiner T. J., Scher A. T., Lipton R.B., J. Headache. Pain., 2005, 6(6), 429

    Article  Google Scholar 

  2. Negro A., Lionetto L., D’Alonzo L., Expert. Opin. Drug Metab. Toxicol., 2013, 9(5), 637

    Article  CAS  Google Scholar 

  3. Diaz-Insa S., Goadsby P. J., Zanchin G., Int. J. Neurosci., 2011, 121(12), 655

    Article  CAS  Google Scholar 

  4. Lionetto L., Fiorillo M., Martelletti P., Expert Opin. Pharmacother., 2011, 12(15), 2279

    Article  CAS  Google Scholar 

  5. Bussone G., Allais G., Chiara B., Expert Opin. Pharmacother., 2011, 12(12), 1933

    Article  CAS  Google Scholar 

  6. Bartolini M, Giamberardino M. A., Lisotto C., J. Headache. Pain., 2011, 12(3), 361

    Article  CAS  Google Scholar 

  7. Satyanarayana C., Ramanjeneyulu G. S., A Process for the Preparation of Almotriptan, WO 2007013098A, 2007

    Google Scholar 

  8. Slassi A., Edwards L., Meng Q. C., 5-Cyclo Indole Compounds, US 5998438, 1999

    Google Scholar 

  9. Bosch J., Roca T., Armengol M., Fernandez-Forner D., Tetrahedron, 2001, 57(6), 1041

    Article  CAS  Google Scholar 

  10. Mubeen K., A Novel Process for the Preparation of Rizatriptan and Intermediates Thereof, Indian Patent 2008MU01252, 2010

    Google Scholar 

  11. Sanz A., Carril A. M. G., Matia M. P., Novella J. L., Alvarez-Builla J., ARKIVOC, 2008, (ii), 53

    Google Scholar 

  12. Bahrami K., Khodaei M. M., Soheilizad M., Tetrahedron Lett., 2010, 51(37), 4843

    Article  CAS  Google Scholar 

  13. Hojat V., Ramin G. V., Saba H., Jafar M., Synletter, 2011, (16), 2315

    Google Scholar 

  14. Bahrami K., Khodaei M. M., Abbasi J., Tetrahedron, 2012, 68(25), 5095

    Article  CAS  Google Scholar 

  15. Bahrami K., Khodaei M. M., Soheilizad M., J. Org. Chem., 2009, 74(24), 9287

    Article  CAS  Google Scholar 

  16. Cheng X., Li X. L., Wan W. L., Hao W. M., Hai L., Wu Y., Chem. Res. Chinese Universities, 2015, 31(1), 53

    Article  CAS  Google Scholar 

  17. Lee J. C., Yu Y. Y., Method for Preparing Migraine Resistant Medicine Almotriptan, CN 102775391, 2012

    Google Scholar 

  18. Waite D. C., Process for the Production of Indole Derivatives, WO 9902493, 1999

    Google Scholar 

  19. Zeevaart J. G., Parkinson C. J., Koning C. B., Tetrahedron Lett., 2005, 46(10), 1597

    Article  CAS  Google Scholar 

  20. Rene O., Fauber B.P., Malhotra S., Yajima H., Org. Lett., 2014, 16(13), 3468

    Article  CAS  Google Scholar 

  21. Choi J., Martin-Gago P., Fu G. C., Liu J., J. Am. Chem. Soc., 2014, 136(34), 12161

    Article  CAS  Google Scholar 

  22. Luzung M. R., Patel J. S., Yin J. J., J. Org. Chem., 2010, 75(23), 8330

    Article  CAS  Google Scholar 

  23. Zhou G., Ting P., Aslanian R., John J., Org. Lett., 2008, 10(12), 2517

    Article  CAS  Google Scholar 

  24. Liu J., Deng Y., Wang H. B., Zhang H., Yu G. X., Wu B. B., Zhang H., Li Q., Marder T. B., Yang Z., Lei A. W., Org. Lett., 2008, 10(11), 2661

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory of Drug-Targeting and Drug-Delivery Systems of Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China

    Xiaolong Li, Rui Qiu, Weili Wan, Xu Cheng, Yi He, Li Hai & Yong Wu

Authors
  1. Xiaolong Li
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  2. Rui Qiu
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  3. Weili Wan
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  4. Xu Cheng
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  5. Yi He
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  6. Li Hai
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  7. Yong Wu
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Corresponding author

Correspondence to Yong Wu.

Additional information

Supported by the National Natural Science Foundation of China(Nos.81373259, 81102324).

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Li, X., Qiu, R., Wan, W. et al. Synthesis of 5-(sulfamoylmethyl)indoles by mild Negishi coupling and their application in almotriptan. Chem. Res. Chin. Univ. 31, 539–542 (2015). https://doi.org/10.1007/s40242-015-5030-5

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  • DOI: https://doi.org/10.1007/s40242-015-5030-5

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