Journal
ORGANIC LETTERS
Volume 12, Issue 22, Pages 5182-5185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102216x
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Funding
- National Institutes of Health [HG005033, GM079590, GM081261]
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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.
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