Efficient Synthesis of a GABAA α2,3-Selective Allosteric Modulator via a Sequential Pd-Catalyzed Cross-Coupling Approach
| Autor: | Wenjie Li, Gary Javadi, Dongwei Cai, Robert D. Larsen, Mark S. Jensen, R. Scott Hoerrner, Dorian P. Nelson, Peter G. Dormer |
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| Rok vydání: | 2005 |
| Předmět: |
Allosteric modulator
Molecular Structure Propanols Pyridines Stereochemistry Organic Chemistry Imidazoles Regioselectivity Stereoisomerism Boronic Acids Chemical synthesis Catalysis chemistry.chemical_compound Pyrimidines Allosteric Regulation Suzuki reaction chemistry Yield (chemistry) Heck reaction Pyridine GABA Agonists Oxidation-Reduction Palladium Boronic acid |
| Zdroj: | The Journal of Organic Chemistry. 70:6034-6039 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo050741o |
| Popis: | A practical synthesis of 2-[3-(4-fluoro-3-pyridin-3-yl-phenyl)-imidazo[1,2-a]pyrimidin-7-yl]-propan-2-ol (1), an oral GABA(A) alpha(2/3)-selective agonist, is described. The five-step process, which afforded 1 in 40% overall yield, included imidazopyrimidine 2 and pyridine boronic acid 4 as key fragments. The synthesis is highlighted by consecutive Pd-catalyzed coupling steps to assemble the final free base 1 in high yield and regioselectivity. A novel method for Pd removal in the final step is also described. |
| Databáze: | OpenAIRE |
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