Poster Presentation RACI Biomolecular Division Conference 2013

Application of flow hydrogenation to medicinal chemistry (#62)

Peter Cossar 1 , Adam McCluskey 1
  1. Chemistry, Centre for Chemical Biology, School of Environmental & Life Sciences, University of Newcastle, Callaghan, NSW, Australia

Flow chemistry systems are becoming an integral part of many medicinal chemistry laboratories. This ‘new technology’ offers multiple benefits over traditional batch approaches, especially in rapid reaction optimisation, improved yields, and ease of scale up. Within the Australian Cancer Research Foundation Centre for Kinomics Flow chemistry Laboratory we have access to a wide array of flow technologies.  In our lead development studies, the ThalesNano H-Cube® and H-CubePro® offer a considerable degree of safety enhancements and reaction versatility. Efficiency enhancements are delivered through rapid modification of hydrogenation pressure, solvent choice, temperature, catalyst and flow rate (residence time).

This presentation examines our groups use of flow hydrogenation approaches. These include reduction of alkyne, olefin, nitrile,1 azide and nitro functional groups, as well as  dehalogenation, ,1,2 debenzylation and reductive amination reactions.3 These transformations can be rapidly optimised using the H-cube®via manipulation of pressure, temperature,solvent and choice of catalyst.

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Figure 1: The scope of reactions possible in the H-cube continuous flow hydrogenation reactor.4

  1. Tarleton, M.; McCluskey, A. Tetrahedron Letters 2011, 52, 1583–1586.
  2. Gordon, C. P.; Venn-Brown, B.; Robertson, M. J.; Young, K. a; Chau, N.; Mariana, A.; Whiting, A.; Chircop, M.; Robinson, P. J.; McCluskey, A. Journal of medicinal chemistry 2013, 56, 46–59.
  3. Gordon, C. P.; Byrne, N.; McCluskey, A. Green Chemistry 2010, 12, 1000.
  4. The H-Cube product series is available from Thales Nanotech- nology Inc. (Budapest, Hungary). For further information, please refer to http://www.thalesnano.com.