Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling

Molecules. 2018 Jan 12;23(1):149. doi: 10.3390/molecules23010149.


The cyclin-dependent kinase inhibitor, CAN508, was protected with di-tert-butyl dicarbonate to access the amino-benzoylated pyrazoles. The bromo derivatives were further arylated by Suzuki-Miyaura coupling using the XPhos Pd G2 pre-catalyst. The coupling reaction provided generally the para-substituted benzoylpyrazoles in the higher yields than the meta-substituted ones. The Boc groups were only utilized as directing functionalities for the benzoylation step and were hydrolyzed under conditions of Suzuki-Miyaura coupling, which allowed for elimination of the additional deprotection step.

Keywords: Boc-protection; CDK inhibitor; Suzuki-Miyaura reaction; XPhos Pd G2; acylation; pyrazole.

MeSH terms

  • Acylation
  • Azo Compounds / chemistry*
  • Catalysis
  • Hydrolysis
  • Molecular Structure
  • Palladium / chemistry
  • Protein Kinase Inhibitors / chemistry*
  • Pyrazoles / chemistry*


  • Azo Compounds
  • CAN 508
  • Protein Kinase Inhibitors
  • Pyrazoles
  • Palladium