Synthesis of Carboxy ATTO 647N Using Redox Cycling for Xanthone Access
James L Bachman1, Cyprian I Pavlich1, Alexander J Boley1
1Department of Chemistry , The University of Texas at Austin , Austin , Texas 78712 , United States.
Abstract:
A synthesis of the carbopyronine dye Carboxy ATTO 647N from simple materials is reported. This route proceeds in 11 forward steps from 3-bromoaniline with the key xanthone intermediate formed using a new oxidation methodology. The step utilizes an oxidation cycle with base, water, iodine, and more than doubles the yield of the standard permanganate oxidation methodology, accessing gram-scale quantities of this late-stage product. From this, Carboxy ATTO 647N was prepared in only four additional steps. This facile route to a complex fluorophore is expected to enable further studies in fluorescence imaging.
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