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Synfacts 2010(3): 0269-0269  
DOI: 10.1055/s-0029-1219300
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Potential mGluR1 Antagonist

Contributor(s): Philip Kocienski
T. Tsuritani*, H. Mizuno*, N. Nonoyama, S. Kii, A. Akao, K. Sato, N. Yasuda, T. Mase
Banyu Pharmaceutical Co. Ltd., Ibaraki, Japan and Merck & Co. Inc., Rahway, USA
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

Schizophrenia afflicts about 1% of the population over the age of 18. The target 1,4-diaryl-5-methyl-1,2,3-triazole is a potent and selective mGluR1 antagonist being developed as a novel treatment for schizophrenia. The key step is a dipolar cycloaddition of the arylazide C to propynylmagnesium chloride (click chemistry) to generate the metallated triazole D. After transmetallation to the zinc reagent E, a Negishi coupling with the bromoarene F gave the target molecule.