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Small molecule library synthesis using segmented flow.

Christina M Thompson1, Jennifer L Poole, Jeffrey L Cross

  • 1Medinical Chemistry Technologies, Abbott Laboratories, Global Pharmaceutical Research and Development, Abbott Park, IL 60064, USA. Christina.m.thompson@abbott.com

Molecules (Basel, Switzerland)
|November 4, 2011
PubMed
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This study introduces a novel flow chemistry method for synthesizing compound libraries. This technique uses fluorous immiscible solvents to efficiently create diverse small molecules in less time than traditional methods.

Area of Science:

  • Organic synthesis
  • Chemical engineering
  • Materials science

Background:

  • Flow chemistry offers a safe, efficient, and scalable platform for synthesizing diverse molecules.
  • Current methods for library synthesis can be time-consuming and resource-intensive.
  • There is a need for rapid and efficient methods to generate small quantities of diverse compounds.

Purpose of the Study:

  • To adapt flow chemistry for the parallel synthesis of compound libraries.
  • To utilize fluorous immiscible solvents as spacers to enable sequential reactions within a single flow system.
  • To validate the methodology through the synthesis of small heterocycle-containing libraries.

Main Methods:

  • Development of a flow chemistry protocol utilizing fluorous immiscible solvents.

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  • Sequential reaction execution within a single flow system without intermediate purification.
  • Synthesis of two small heterocycle-containing libraries on a 0.2 mmol scale.

    • Main Results:

    • Successful synthesis of compound libraries using the developed flow chemistry method.
    • Generation of tens of milligrams of material per reaction plug.
    • Achieved library synthesis in half the time compared to conventional microwave synthesis, with comparable yields.

    Conclusions:

    • The fluorous solvent-mediated flow chemistry approach enables rapid and efficient synthesis of compound libraries.
    • This methodology is ideal for quickly generating small quantities of diverse compounds for screening and discovery.
    • The technique offers a significant time advantage over traditional microwave-assisted synthesis for library generation.