The Synthesis of a Rotationally Restricted Phenolic Analog of 5-Methoxy-3-(1,2,5,6-tetrahydropyrid-4-yl)indole (RU-24,969)

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