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DOI: 10.1055/s-2007-1000855
A Convenient Synthesis of 1-(4-Fluorophenyl)-2-(4-pyridyl)cyclopentene from Cyclopentanone
Publication History
Publication Date:
18 December 2007 (online)
Abstract
In the framework of investigating the role of pyridyl-substituted five-membered heterocycles as potential p38 mitogen-activated protein kinase inhibitors, we synthesized the disubstituted carbocyclic analogue, 1-(4-fluorophenyl)-2-(4-pyridyl)cyclopentene. A multistep synthesis of this compound starting from cyclopentanone is reported. Cyclopentanone was converted into 1-cy-clopentenyl-4-fluorobenzene using a Grignard reaction. The oxidation of this product with hydrogen peroxide and formic acid gave 2-(4-fluorophenyl)cyclopentanone. This ketone was activated using a neodymium salt (NdCl3·2LiCl) and subsequently reacted with a complexed Grignard reagent (pyMgCl·LiCl) to give the corresponding cyclopentanol derivative. Finally, dehydration of the latter alcohol led to the title compound.
Key words
Grignard reactions - carbocycles - medicinal chemistry - neodymium salt - inhibitors
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