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Communication | Regular issue | Vol 31, No. 5, 1990, pp.805-809
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5377
The Synthesis of a Rotationally Restricted Phenolic Analog of 5-Methoxy-3-(1,2,5,6-tetrahydropyrid-4-yl)indole (RU-24,969)

John E. Macor* and Michael E. Newman

*Department of Medical Chemistry, Central Research Division, Pfizer Inc., Groton, Connecticut 06355, U.S.A.


Pyrrolo[3,2-b]pyrid-5-one represents a rotationally restricted phenolic analog of 5-hydroxyindole. The synthesis of the rotationally restricted phenolic analog of the serotonin agonist, 5-methoxy-3-(1,2,5,6-tetrahydropyrid-4-yl)indole (RU-24,969), is presented. Protection of the 2-pyridone in this synthesis was achieved using its t-butyl ether.