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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 21
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Original Articles

Convenient Synthesis of tert‐Butyl Esters of Indole‐5‐carboxylic Acid and Related Heterocyclic Carboxylic Acids

, &
Pages 3117-3123 | Received 08 Mar 2006, Published online: 24 Nov 2006
 

Abstract

The tert‐butyl esters of indole‐5‐carboxylic acid and related compounds such as benzofuran‐ and benzothiophene‐5‐carboxylic acid were readily accessed by reacting the appropriate carboxylic acids with tert‐butyl trichloroacetimidate. To obtain the tert‐butyl esters of the 5‐carboxylic acids of 1H‐benzotriazole and 1H‐benzimidazole, position 1 of these heterocycles had to be protected by acetylation prior to reaction with tert‐butyl trichloroacetimidate. Cleavage of the acetyl residue of the obtained intermediates by dilute aqueous NaOH in ethanol led to the desired tert‐butyl 1H‐benzotriazole‐and 1H‐benzimidazole‐5‐carboxylates.

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