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Communication | Special issue | Vol 37, No. 3, 1994, pp.1447-1450
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S71
A Short Synthesis of a Conformationally Restricted Analog of the Neurotransmitter Serotonin with Reduced Basicity

John E. Macor* and Kevin Ryan

*Department of Medical Chemistry, Central Research Division, Pfizer Inc., Eastern Point Road, Groton, Connecticut 06340, U.S.A.

Abstract

The synthesis of a less basic, conformationally restricted analog of serotonin is described [2-(5-methoxyindol-3-ylmethyl)imidazole (1)]. The crucial carbon-carbon bond formation step in this synthesis involves the attack of a 2-lithioimidazole anion on an indole-3-carboxaldehyde derivative.