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Synthesis of 14C-labeled 4-hydroxyindole as an intermediate for the preparation of (S)-2-[4-[2-[3-(indol-2-[14C]-4-yloxy)-2-hydroxypropylamino]-2-methylpropyl]-phenoxy]pyridine-5-carboxamide (LY368842-[indole-14C]) glycolate

✍ Scribed by Boris A. Czeskis; Dean K. Clodfelter; William J. Wheeler

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
102 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Synthesis of 4‐hydroxyindole labeled with ^14^C at the 2‐position was accomplished based on the vicarious nucleophilic substitution reaction of benzyl‐protected 3‐nitrophenol with p‐chlorophenoxyacetonitrile‐[1‐^14^C]. This was followed by the reductive cyclization of o‐nitrocyanomethyl derivative by palladium catalyzed hydrogenation. p‐Chlorophenoxyacetonitrile‐[1‐^14^C] was prepared from commercially available p‐chlorophenoxymethyl chloride and sodium cyanide‐[^14^C]. 4‐Hydroxyindole‐[2‐^14^C] was used for the synthesis of ^14^C‐labeled β~3~ adrenergic agonist LY368842. Copyright © 2002 John Wiley & Sons, Ltd.

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