A straightforward synthetic approach for roxindole.
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.
Lange
J H
JH
Solvay Pharmaceuticals Research Laboratories, Department of Medicinal Chemistry, Weesp, The Netherlands. jos.lange@solvay.com
de Jong
J C
JC
Sanders
H J
HJ
Visser
G M
GM
Kruse
C G
CG
D018491:Dopamine Agonists / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D000078183:Oxindoles; D011725:Pyridines / Q000138:chemical synthesis*; D013387:Succinic Anhydrides / Q000737:chemistry
C119495:5-methoxyindolylmagnesium bromide; D018491:Dopamine Agonists; D007211:Indoles; D009942:Organometallic Compounds; D000078183:Oxindoles; D011725:Pyridines; D013387:Succinic Anhydrides; C059613:roxindole; C031801:succinic anhydride