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Synthesis and characterization of tritium labeled 2,3,4,9-tetrahydro-1H-carbazoles as potent DP receptor antagonists

✍ Scribed by Carl Berthelette; Michael J. Boyd; Nicolas Lachance; Bruno Roy; Claudio F. Sturino; John Scheigetz; Robert J. Zamboni

Publisher
John Wiley and Sons
Year
2004
Tongue
French
Weight
109 KB
Volume
47
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Tritium labeled 2,3,4,9‐tetrahydro‐1__H__‐carbazole 1a and 2a were prepared in good yields with a specific activity of 7.0 Ci/mmol (214 GBq/mmol) and 4.2 Ci/mmol (155 GBq/mmol), respectively. Both compounds have been synthesized in high radiochemical purity by catalytic tritium–bromine exchange of the corresponding aryl bromide precursors. The 6‐bromocarbazole precursors 7 and 8 were prepared as a mixture by a three step process, involving regioselective bromination of 3c with pyridinium tribromide, oxidation of thioether 4c using m‐CPBA and hydrolysis of acylsultamcarbazole 5c. Finally, HPLC separation of the enantiomers afforded the 6‐bromo precursors 7 and 8 in high diastereomeric ratio (dr 99% and dr 93% respectively). Copyright © 2004 John Wiley & Sons, Ltd.

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