One-Step Continuous Flow Synthesis of Highly Substituted Pyrrole-3-carboxylic Acid Derivatives via in Situ Hydrolysis of tert-Butyl Esters

The first one-step, continuous flow synthesis of pyrrole-3-carboxylic acids directly from tert-butyl acetoacetates, amines, and 2-bromoketones is reported. The HBr generated as a byproduct in the Hantzsch reaction was utilized in the flow method to hydrolyze the t-butyl esters in situ to provide the...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 22; pp. 5182 - 5185
Main Authors Herath, Ananda, Cosford, Nicholas D. P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.11.2010
Amer Chemical Soc
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Summary:The first one-step, continuous flow synthesis of pyrrole-3-carboxylic acids directly from tert-butyl acetoacetates, amines, and 2-bromoketones is reported. The HBr generated as a byproduct in the Hantzsch reaction was utilized in the flow method to hydrolyze the t-butyl esters in situ to provide the corresponding acids in a single microreactor. The protocol was used in the multistep synthesis of pyrrole-3-carboxamides, including two CB1 inverse agonists, directly from commercially available starting materials in a single continuous process.
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol102216x