Unusual reactivity of 2-amino-1H-indole-3-carboxylate esters

Riseley, Ross, Carneiro, Aitor, Mu, Zhilin, Alkahtani, Rawiyah, Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Waller-Evans, Helen ORCID: https://orcid.org/0000-0003-4133-6064 and Jones, D. Heulyn 2025. Unusual reactivity of 2-amino-1H-indole-3-carboxylate esters. ARKIVOC 2025 (5) , 202512417. 10.24820/ark.5550190.p012.417

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Abstract

We report the outcome of the attempted synthesis of amino-1H-indole-3-carboxylic acid from the corresponding ethyl and tert-butyl esters. Subjection of the tert-butyl ester to acidic conditions led to quantitative conversion to indolin-2-imine hydrochloride and the ethyl ester to basic conditions led to a ring-opened product, showing that the carboxylic acid is not easily-accessible via the corresponding esters. During the synthesis of the esters, the novel compound 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)phenol was isolated and was shown to be chiral due to atropisomerism.

Item Type:	Article
Date Type:	Publication
Schools:	Schools > Chemistry Schools > Biosciences
Publisher:	ARKAT USA
ISSN:	1551-7012
Funders:	Coleg Cymraeg Cenedlaethol, Harrington Institute
Date of First Compliant Deposit:	1 October 2025
Date of Acceptance:	25 July 2025
Last Modified:	01 Oct 2025 09:45
URI:	https://orca.cardiff.ac.uk/id/eprint/181418

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