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

Molecules

Zdeněk Trávníček¹  Igor Popa¹  Filip Hančík²  Martin Pisár²  Petr Cankař²  Eva Schütznerová³ 

[1] Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech Republic;Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech Republic;Institute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech Republic;

关键词: pyrazole;    Boc-protection;    Suzuki-Miyaura reaction;    acylation;    CDK inhibitor;    XPhos Pd G2;   

DOI  :  10.3390/molecules23010149

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown