Journal
RSC ADVANCES
Volume 12, Issue 41, Pages 26497-26503Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra05132j
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Funding
- Alzheimer's Research UK (ARUK)
- Alzheimer's Drug Discovery Foundation (ADDF)
- Alzheimer's Research UK [560832]
- Alzheimer's Drug Discovery Foundation
- Harrington Discovery Institute at University Hospitals in Cleveland
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In this study, 1-Phenyl-1H-1,2,3-triazole 1 (ARUK3001185) was prepared on a large scale using both copper-catalyzed azide-alkyne cycloaddition (CuAAC) and a Clark modification of the Sakai reaction. The Sakai-Clark method proved to be superior, with operational simplicity, metal-free conditions, and avoiding the use of aryl azide 7. The method was reliable for the large-scale production of >100 g of 1 with good efficiency and high purity.
1-Phenyl-1H-1,2,3-triazole 1 (ARUK3001185) was prepared on large scale from aniline 4 by application of both (1) a copper catalyzed azide-alkyne cycloaddition (CuAAC) with (trimethylsilypacetylene, and (2) a Clark modification of the Sakai reaction. The one-pot Sakai-Clark method with (MeO)(2)CHCH=NNHTos (2b) proved to be superior as it was operationally simple, metal-free, and avoided the use of aryl azide 7. The Sakai-Clark method has been reliably performed on large scale to produce >100 g of 1 in good efficiency and high purity.
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