A straightforward synthetic approach for roxindole.

J H Lange, J C de Jong, H J Sanders, G M Visser, C G Kruse

Solvay Pharmaceuticals Research Laboratories, Department of Medicinal Chemistry, Weesp, The Netherlands. jos.lange@solvay.com

Bioorganic & medicinal chemistry letters 1999 Apr 5

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A concise synthetic approach to the dopamine autoreceptor agonist roxindole 1 has been devised. The key step in the novel route is the addition of succinic anhydride to 5-methoxyindolylmagnesium bromide, which circumvents the cumbersome construction of the indole moiety - via the Japp Klingemann- Fischer indole methodology - in the original route. This novel route will enable a quick, multi-gram synthesis of roxindole from cheap starting materials.

Citation

J H Lange, J C de Jong, H J Sanders, G M Visser, C G Kruse. A straightforward synthetic approach for roxindole. Bioorganic & medicinal chemistry letters. 1999 Apr 5;9(7):1055-6