Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling
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-substitu...
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MDPI AG
2018-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/1/149 |
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| author | Martin Pisár Eva Schütznerová Filip Hančík Igor Popa Zdeněk Trávníček Petr Cankař |
| author_facet | Martin Pisár Eva Schütznerová Filip Hančík Igor Popa Zdeněk Trávníček Petr Cankař |
| author_sort | Martin Pisár |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-17T10:06:27Z |
| format | Article |
| id | doaj.art-d864cfeb490e401796fa5db8fa1feecc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T10:06:27Z |
| publishDate | 2018-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d864cfeb490e401796fa5db8fa1feecc2022-12-21T21:53:09ZengMDPI AGMolecules1420-30492018-01-0123114910.3390/molecules23010149molecules23010149Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura CouplingMartin Pisár0Eva Schütznerová1Filip Hančík2Igor Popa3Zdeněk Trávníček4Petr Cankař5Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech RepublicInstitute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech RepublicDepartment of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech RepublicDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech RepublicDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech RepublicDepartment of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 771 46 Olomouc, Czech RepublicThe 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.http://www.mdpi.com/1420-3049/23/1/149pyrazoleBoc-protectionSuzuki-Miyaura reactionacylationCDK inhibitorXPhos Pd G2 |
| spellingShingle | Martin Pisár Eva Schütznerová Filip Hančík Igor Popa Zdeněk Trávníček Petr Cankař Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling Molecules pyrazole Boc-protection Suzuki-Miyaura reaction acylation CDK inhibitor XPhos Pd G2 |
| title | Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling |
| title_full | Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling |
| title_fullStr | Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling |
| title_full_unstemmed | Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling |
| title_short | Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling |
| title_sort | modification of boc protected can508 via acylation and suzuki miyaura coupling |
| topic | pyrazole Boc-protection Suzuki-Miyaura reaction acylation CDK inhibitor XPhos Pd G2 |
| url | http://www.mdpi.com/1420-3049/23/1/149 |
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