Skip to main content
Log in

Synthesis of 4-aryl(hetaryl)pyrazolo[1,5-a]pyrazines by palladium-catalyzed Suzuki–Miyaura cross coupling

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

4-Bromopyrazolo[1,5-a]pyrazines react with aryl(hetaryl)boronic acids in the presence of catalytic amounts of Pd(dppf)Cl2·CH2Cl2 and an excess of Cs2CO3 in the MeCN–H2O, 9:1 solvent system with the formation of 4-aryl(hetaryl)pyrazolo[1,5-a]pyrazines.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.

    Article  CAS  Google Scholar 

  2. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron. 2002, 58, 9633. (c) Miyaura, N. Top. Curr. Chem. 2002, 219, 11. (d) McConnell, A. J.; Beer, P. D. Angew. Chem., Int. Ed. 2012, 51, 5052. (e) Li, H.; Seechurn, C. C. C. J.; Colacot, T. J. ACS Catal. 2012, 2, 1147. (f) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. (g) Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270. (h) Maluenda, I.; Navarro, O. Molecules. 2015, 20, 7528. (i) Chatterjee, A.; Ward, T. R. Catal. Lett. 2016, 146, 820. (j) Hooshmand, S. E.; Heidari, B.; Sedghi, R.; Varma, R. S. Green Chem. 2019, 21, 381.

  3. (a) Ronga, L.; Del Favero, M.; Cohen, A.; Soum, C.; Le Pape, P.; Savrimoutou, S.; Pinaud, N.; Mullié, C.; Daulouede, S.; Vincendeau, P.; Farvacques, N.; Agnamey, P.; Pagniez, F.; Hutter, S.; Azas, N.; Sonnet, P.; Guillon, J. Eur. J. Med. Chem. 2014, 81, 378. (b) Tan, J.; Chen, Y.; Li, H.; Yasuda, N. J. Org. Chem. 2014, 79, 8871. (c) Petrera, M.; Wein, T.; Allmendinger, L.; Sindelar, M.; Pabel, J.; Höfner, G.; Wanner, K. T. Chem. Med. Chem. 2016, 11, 519. (d) Zhang, Y.; Banwell, M. G.; Carr, P. D.; Willis, A. C. Org. Lett. 2016, 18, 704. (e) Driowya, M.; Saber, A.; Marzag, H.; Demange, L.; Bougrin, K.; Benhida, R. Molecules 2016, 21, 1032. (f) Hamdy, A. M.; Khaddour, Z.; Al-Masoudi, N. A.; Rahman, Q.; Hering-Junghans, C.; Villinger, A.; Langer, P. Bioorg. Med. Chem. 2016, 24, 5115. (g) Sarkar, U.; Hillebrand, R.; Johnson, K. M.; Cummings, A. H.; Phung, N. L.; Rajapakse, A.; Zhou, H.; Willis, J. R.; Barnes, C. L.; Gates, K. S. J. Heterocycl. Chem. 2017, 54, 155. (h) Jafari, B.; Ospanov, M.; Ejaz, S. A.; Yelibayeva, N.; Khan, S. U.; Amjad, S. T.; Safarov, S.; Abilov, Z. A.; Turmukhanova, M. Zh.; Kalugin, S. N.; Ehlers, P.; Lecka, J.; Sévigny, J.; Iqbal, J.; Langer, P. Eur. J. Med. Chem. 2018, 144, 116. (i) Pedron, J.; Boudot, C.; Bourgeade-Delmas, S.; Sournia-Saquet, A.; Paloque, L.; Rastegari, M.; Abdoulaye, M.; El-Kashef, H.; Bonduelle, C.; Pratviel, G.; Wyllie, S.; Fairlamb, A. H.; Courtioux, B.; Verhaeghe, P.; Valentin, A. ChemMedChem 2018, 13, 2217. (j) Pomarański, P.; Roszkowski, P.; Maurin, J. K.; Budzianowski, A.; Czarnocki, Z. Beilstein J. Org. Chem. 2018, 14, 2384.

  4. Brough, S.; Evans, R.; Luker, T. J.; Raubo, P. WO Patent 2009001132.

  5. Botton, G.; Valeur, E.; Charon, C.; Kergoat, M.; Elbawab, S. WO Patent 2009132739.

  6. Burkamp, F.; Hansen, P.; Hossain, N.; Lisius, A.; Lönn, H.; Lundkvist, M. WO Patent 2009058076.

  7. Botton, G.; Valeur, E.; Kergoat, M.; Charon, C.; Elbawab, S. WO Patent 2009109258.

  8. Botton, G.; Valeur, E.; Kergoat, M.; Charon, C.; Elbawab, S. WO Patent 2009109341.

  9. Liu, K. K.-C.; Bagrodia, S.; Bailey, S.; Cheng, H.; Chen, H.; Gao, L.; Greasley, S.; Hoffman, J. E.; Hu, Q.; Johnson, T. O.; Knighton, D.; Liu, Z.; Marx, M. A.; Nambu, M. D.; Ninkovic, S.; Pascual, B.; Rafidi, K.; Rodgers, C. M.-L.; Smith, G. L.; Sun, S.; Wang, H.; Yang, A.; Yuan, J.; Zou, A. Bioorg. Med. Chem. Lett. 2010, 20, 6096.

    Article  CAS  Google Scholar 

  10. Goel, R.; Luxami, V.; Paul, K. RSC Adv. 2014, 4, 9885.

    Article  CAS  Google Scholar 

  11. Tasker, A.; Pettus, L. H.; Wurz, R. WO Patent 2009117156.

  12. Allen, S.; Boys, M. L.; Chicarelli, M. J.; Fell, J. B.; Fischer, J. P.; Gaudino, J.; Hicken, E. J.; Hinklin, R. J.; Kraser, C. F.; Laird, E.; Robinson, J. E.; Tang, T. P.; Burgess, L. E.; Rieger, R. A.; Pheneger, J.; Satoh, Y.; Leftheris, K.; Raheja, R. K.; Bennett, B. L. Patent WO 2016090285.

  13. Zorina, A. D.; Nikiforova, N. S.; Zarubaev, V. V.; Marchenko, S. A.; Selivanov, S. I.; Starova, G. L.; Mehtiev, A. R.; Rodionov, E. I.; Rodionova A. A.; Trifonov, R. E. Mendeleev Commun. 2019, 29, 500.

    Article  CAS  Google Scholar 

  14. Qi, H.; Choi, S.; Dakka, A; Karp, G. M.; Narasimhan, J.; Naryshkin, N.; Turpoff, A. A.; Weetall, M. L.; Welch, E.; Woll, M. G.; Yang, T.; Zhang, N; Zhang, X.; Zhao, X.; Green, L.; Pinard, E.; Ratni, H. WO Patent 2013119916.

  15. Hrynyshyn, Ye. V.; Tsizorik, N. M.; Musiychuk, A. R.; Bol'but, A. V.; Vovk, M. V. Chem. Heterocycl. Compd. 2017, 53, 1242. [Khim. Geterotsikl. Soedin. 2017, 53, 1242.]

  16. Woll, M. G.; Qi, H.; Turpoff, A.; Zhang, N.; Zhang, X.; Chen, G.; Li, C.; Huang, S.; Yang, T.; Moon, Y.-C.; Lee, C.-S.; Choi, S.; Almstead, N. G.; Naryshkin, N. A.; Dakka, A.; Narasimhan, J.; Gabbeta, V.; Welch, E.; Zhao, X.; Risher, N.; Sheedy, J.; Weetall, M.; Karp, G. M. J. Med. Chem. 2016, 59, 6070.

    Article  CAS  Google Scholar 

  17. (a) Liverton, N.; Kuduk, S. D.; Beshore, D. C.; Meng, N.; Luo, Y. WO Patent 2016106106. (b) Liverton, N.; Kuduk, S. D.; Beshore, D. C.; Meng, N.; Luo, Y. WO Patent 2016101119. (c) Pasternak, A.; Pio, B.; Chobanian, H. R.; Shi, Z.-C.; Dong, S.; Guo, Y.; Walsh, S. P.; Guo, Z.; Ferguson, R. D.; Cato, B. WO Patent 2016060941.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yevhenii V. Hrynyshyn.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hrynyshyn, Y.V., Musiychuk, A.R., Tsizorik, N.M. et al. Synthesis of 4-aryl(hetaryl)pyrazolo[1,5-a]pyrazines by palladium-catalyzed Suzuki–Miyaura cross coupling. Chem Heterocycl Comp 55, 1070–1074 (2019). https://doi.org/10.1007/s10593-019-02579-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02579-2

Keywords

Navigation