6-Br-ICA-OEt is an amino acid derivative related to indole-3-carboxylic acid (ICA) bearing a bromine substituent at the 6-position and an ethyl ester at the carboxyl terminus, with the amino functionality present as part of the derivative's overall amino acid framework. The molecule contains an indole ring that provides a conjugated aromatic system and a brominated electrophilic site, while the carboxyl group is masked as an O-ethyl ester (-COOEt) rather than existing as a free carboxylic acid, which changes hydrogen-bonding and reactivity relative to the corresponding free amino acid. In synthesis and chemical biology workflows, this ester form is commonly used as a protected/derivatized intermediate for preparing further substituted ICA analogues, generating labeled or conjugatable derivatives, or supporting peptide- and amide-building steps where controlled carboxyl reactivity is required.
CAT No: CP25127
CAS No:103858-53-3
Synonyms/Alias:103858-53-3;ethyl6-bromo-1H-indole-2-carboxylate;ETHYL6-BROMOINDOLE-2-CARBOXYLATE;6-Bromoindole-2-carboxylicacidethylester;6-bromo-1H-indole-2-carboxylicacidethylester;6-Bromo-2-(ethoxylcarbonyl)-1H-indole;6-BROMO-2-CARBETHOXYINDOLE;6-BROMO-2-CARBOETHOXYINDOLE;6-Bromo-2-Indolecarboxylicethylester;AR-437/43285096;1H-Indole-2-carboxylicacid,6-bromo-,ethylester;ZINC02383949;ACMC-209znl;AC1Q349W;SCHEMBL3275836;CTK4A2445;FVMZWWFKRMBNSZ-UHFFFAOYSA-N;MolPort-002-041-340;ZINC2383949;ANW-50479;CE-165;MFCD03094942;AKOS004912416;AS06045;CM13590
6-Br-ICA-OEt is a bromo-substituted indole-3-carboxylic acid ethyl ester derivative designed for downstream chemical elaboration rather than direct incorporation into peptides. The ethyl ester functionality provides a convenient handle for conversion to other carboxylate-reactive forms, while the 6-bromo substituent enables selective cross-coupling and other aryl functionalization strategies in medicinal chemistry and heteroaromatic scaffold development. In chemical biology and pharmaceutical intermediate workflows, this type of halogenated indole ester is commonly used as a modular building block to access analog series with controlled substitution patterns.
1. Medicinal Chemistry Intermediates
6-Br-ICA-OEt is frequently used as a halogenated indole carboxylate building block in medicinal chemistry programs that require rapid diversification of the indole ring substitution pattern. Research groups developing small-molecule libraries leverage the 6-bromo handle for coupling-based installation of new aryl or heteroaryl groups, while the ester form supports conversion into alternative carboxylic acid derivatives needed for structure-activity relationship (SAR) exploration. Pharmaceutical intermediate development teams also favor this scaffold form because it integrates two practical transformation points—aryl functionalization at the bromo position and carboxylate interconversion from the ethyl ester—within a single, well-defined starting material.
2. Indole Scaffold Diversification
6-Br-ICA-OEt supports parallel synthesis workflows aimed at generating substituted indole analogs for lead optimization and chemical probe discovery. Synthetic chemistry teams use the bromo substituent as a reliable functional group for late-stage diversification, enabling access to a range of substituted indoles without changing the core indole-3-carboxylate motif. The ethyl ester is particularly useful when downstream steps require temporary protection of the carboxyl group to improve handling during multi-step sequence assembly, allowing the indole framework to be modified while maintaining a consistent carboxylate functionality for later conversion.
3. Cross-Coupling Building Block
6-Br-ICA-OEt is well matched to coupling-driven synthesis strategies where aryl bromides serve as electrophilic partners to introduce new substituents onto the indole core. Medicinal chemistry and process development groups often select this kind of bromo-ester intermediate to build analog series efficiently, because the indole's substitution pattern can be tuned while preserving the ester-bearing carboxylate functionality for subsequent derivatization. This makes the reagent a practical choice for constructing heteroaromatic frameworks used in small-molecule discovery, including intermediates that later require conversion to acids, amides, or other activated carboxyl derivatives.
4. Carboxylate Derivative Preparation
6-Br-ICA-OEt is used in intermediate manufacturing and research synthesis when the ethyl ester must be carried through early steps and then transformed into more reactive or more structurally specific carboxylate derivatives. Chemical development teams commonly route the ester into downstream acid-based or acyl-functional intermediates to support amide formation, salt generation, or other carboxyl group elaboration required for final target assembly. By keeping the carboxyl group in an ester form during scaffold modification, 6-Br-ICA-OEt helps streamline multi-functional intermediate sequences where both the aromatic substitution site and the carboxyl functionality must be controlled independently.
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