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High Yield SNAr Substitution Reaction of (Hetero)Aryl Chlorides in a MicroFluidic Reactor
EP26896
Poster Title: High Yield SNAr Substitution Reaction of (Hetero)Aryl Chlorides in a MicroFluidic Reactor
Submitted on 30 Jan 2018
Author(s): Mohammad Parvez Alam, Barbara Jagodzinska, Jesus Campagna, Patricia Spilman and Varghese John
Affiliations: Drug Discovery Laboratory, Department of Neurology, Easton Center for AD Research, UCLA
Poster Views: 827
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Poster Information
Abstract: Use of flow microreactor has quite effectively decreased the reaction time of C-O
bond (aryl or alkyl) formation. This methodology should facilitate the synthesis of
alkyl/aryl ethers in a continuous approach and can be coupled with number of other
microreactors as required by the synthetic scheme to advance further and aid in the
discovery of new drug candidates. Additional efforts toward C-O bond formation in
pyridine and other pyrimidines are under progress and will be reported in due
course.

High Yield SNAr Substitution Reaction of HeteroAryl Chlorides in a Microfluidic Reactor” received the sole award from ePosters, one of the sponsors of the Flow Chemistry Congress. The work that resulted in the presentation was funded by the Mary S. Easton Center for Alzheimer’s Disease Research, Department of Neurology, David Geffen School of Medicine, UCLA. Dr. Alam utilized a Syrris microflow reactor to overcome some of the obstacles to continuous chemical synthesis of active pharmaceutical ingredients (API). This new method will not only allow continuous, high-yield of new compounds, it is also considered “Green Chemistry” and part of the emerging field of Flow Chemistry, the focus of the Congress.
Summary: This methodology facilitates the synthesis of alkyl/aryl ethers in a continuous approach and can be coupled with number of other microreactors as required by the synthetic scheme to advance further and aid in the discovery of new drug candidates. References: 1) (a) Buckingham, J. Dictionary of Natural Products; University Press: Cambridge, MA, 1994. (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345. (c) Sawyer, J. S. Tetrahedron, 2000, 56, 5045. (d) Thomas, A. W.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 5400.

2) Ullman, F. Chem. Ber. 1904, 37, 853.

3) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.

4) Walsh, K.; Sneddon, H. F. and Moody, C. J. RSC Adv., 2014, 4, 28072.

5) Traore, T.; Cavagnino, A.; Saettel, N.; Radvanyi, F.; Piguel, S.; Pierrot, I.; Stoven, V. and Legraverend, M. Eur. J. Med. Chem. 2013, 70, 789.
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