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

ABSTRACT: 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.

SUBMITTER: Pisar M

PROVIDER: S-EPMC6017724 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Pisár Martin M Schütznerová Eva E Hančík Filip F Popa Igor I Trávníček Zdeněk Z Cankař Petr P

Molecules (Basel, Switzerland) 20180112 1

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 hydroly ...[more]

PMID: 29329219

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