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<p>A Continuous Flow Photochemistry (CFP) - based protocol has been developed for the synthesis of a complex isomeric API impurity, Sulindac <i>E</i>-Isomer (<b>2</b>), which is a USP reference standard. The reported flow photochemical <i>E</i>/<i>Z</i> isomerization reaction is more efficient than metal catalyzed multistep batch process (residence time of 3 min in flow vs overall reaction time of 20 h in batch process; 44% product formation in photocatalytic flow process vs 13.82% in batch isomerization step) and proceeds with a clean reaction profile without any byproduct formation. The improved product formation is attributed to the triplet energy transfer from the photocatalyst and supported by density functional theory (DFT) calculations. The robustness of this approach was demonstrated on a multigram scale providing the potential for future application in the synthesis of isomeric API impurities and enabling USP reference standard development and availability towards ensuring quality and safety of medicines.</p>

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Development of continuous flow photochemistry-based protocol for the synthesis of Sulindac related impurity

  • 期刊论文

  • 发表日期：

    2025年10月17日

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  • Mohamed Takhi,
  • Nagaraju Pallava,
  • Bhushan Mahajan,
  • Prasad Yeragorla,
  • Srinivas Eedubilli,
  • Ranjit Kumar Nethi,
  • Yesudas Kada,
  • Rabin Bera,
  • Koushik Mondal,
  • Lakshmikanth Juluru,
  • Veera Reddy Pinninti,
  • Suresh Kumar Sheik,
  • Rohit Lokhande,
  • Gabriela Grasa Mannino,
  • Rajender Kumar Potlapally,
  • Mrunal Jaywant

摘要

A Continuous Flow Photochemistry (CFP) - based protocol has been developed for the synthesis of a complex isomeric API impurity, Sulindac E-Isomer (2), which is a USP reference standard. The reported flow photochemical E/Z isomerization reaction is more efficient than metal catalyzed multistep batch process (residence time of 3 min in flow vs overall reaction time of 20 h in batch process; 44% product formation in photocatalytic flow process vs 13.82% in batch isomerization step) and proceeds with a clean reaction profile without any byproduct formation. The improved product formation is attributed to the triplet energy transfer from the photocatalyst and supported by density functional theory (DFT) calculations. The robustness of this approach was demonstrated on a multigram scale providing the potential for future application in the synthesis of isomeric API impurities and enabling USP reference standard development and availability towards ensuring quality and safety of medicines.