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Development of a Robust Protocol for the Synthesis of 6-Hydroxybenzofuran-3-carboxylic Acid

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    Development of a Robust Protocol for the Synthesis of 6-Hydroxybenzofuran-3-carboxylic Acid
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    • Isabelle Gallou
      Isabelle Gallou
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
      More by Isabelle Gallou
    • Bernhard Erb
      Bernhard Erb
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Michael Marti
      Michael Marti
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Gian-Luca Nuzzo
      Gian-Luca Nuzzo
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Andreas Jager
      Andreas Jager
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Manuela Seeger
      Manuela Seeger
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Pierre Chassagne
      Pierre Chassagne
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Jonas Aronow
      Jonas Aronow
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Margery Cortes-Clerget
      Margery Cortes-Clerget
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
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    • Fabrice Gallou*
      Fabrice Gallou
      Chemical & Analytical Development, Novartis Pharma AG, CH-4056 Basel, Switzerland
      *E-mail: [email protected]
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      Orcidhttp://orcid.org/0000-0001-8996-6079
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    Organic Process Research & Development

    Cite this: Org. Process Res. Dev. 2020, 24, 5, 861–866
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    https://doi.org/10.1021/acs.oprd.9b00546
    Published January 28, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Benzofuran scaffolds are fundamental moieties found in a variety of biologically active natural products and synthetic drugs. In the course of one of our development programs, we needed to develop a practical and cost-effective manufacturing approach to such a benzofuran scaffold. Here we report a highly robust four-step, one-pot process that provides access to a 6-hydroxybenzofuran-3-carboxylic acid structure. An 1H NMR monitoring study allowed a better understanding of the overall sequence of events and the nature of the detected intermediates. After six steps, including the optimized tandem process, the desired hydroxylated benzofuran was obtained in 40% yield with a purity above 99%.

    Copyright © 2020 American Chemical Society

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    This article is cited by 2 publications.

    1. Guowei Yan, Ji Ma, Simeng Qi, Alexander M. Kirillov, Lizi Yang, Ran Fang. DFT rationalization of the mechanism and selectivity in a gold-catalyzed oxidative cyclization of diynones with alcohols. Physical Chemistry Chemical Physics 2024, 26 (45) , 28484-28494. https://doi.org/10.1039/D4CP01700E
    2. Halina Kwiecień. Five-membered ring systems: furans and benzofurans. 2021, 175-221. https://doi.org/10.1016/B978-0-323-98410-2.00007-2
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    Organic Process Research & Development

    Cite this: Org. Process Res. Dev. 2020, 24, 5, 861–866
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.oprd.9b00546
    Published January 28, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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