Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 183–187 | Cite as

Methylation of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline through Suzuki–Miyaura cross coupling

  • Nour Bou Karroum
  • Cindy Patinote
  • Carine Deleuze-Masquéfa
  • Georges Moarbess
  • Mona Diab-Assaf
  • Pierre Cuq
  • Issam Kassab
  • Pierre-Antoine Bonnet
Article
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The Suzuki–Miyaura cross coupling is a versatile and powerful reaction for carbon–carbon bond formation which nevertheless requires optimization of conditions. While the coupling of arylboron derivatives with aryl or alkenyl halides has been widely explored, alkylation has attracted less attention. We describe herein the methylation of bromo derivatives of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline having biologically interesting structures. As the challenging Suzuki–Miyaura reaction is highly substratedependent, the choices of the base, solvent, and additive are also discussed.

Keywords

imidazo[1,2-a]pyrazine imidazo[1,2-a]quinoxaline pyrazolo[1,5-a]quinoxaline methylation Suzuki–Miyaura cross coupling 

Notes

We would like to thank the Société d’Accélération du Transfert de Technologies (SATT AxLR) for financial support to C.P. and the Lebanese University for financial support to N.B.K. We also thank the French department of Biotage for lending us a HPFC system.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nour Bou Karroum
    • 1
    • 2
  • Cindy Patinote
    • 1
    • 3
  • Carine Deleuze-Masquéfa
    • 1
  • Georges Moarbess
    • 2
  • Mona Diab-Assaf
    • 2
  • Pierre Cuq
    • 1
  • Issam Kassab
    • 2
  • Pierre-Antoine Bonnet
    • 1
  1. 1.IBMM, Université de Montpellier, CNRS, ENSCMMontpellierFrance
  2. 2.Tumorigenèse et Pharmacologie Antitumorale, Lebanese University, EDSTFanar JdeidehLebanon
  3. 3.Société d’Accélération du Transfert de Technologies (SATT AxLR), CSUMontpellierFrance

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