6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester
[CAS# 1256584-75-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester
• Synonyms: tert-butyl 6-cyano-2-[2-(4-ethyl-3-iodophenyl)propan-2-yl]-1H-indole-3-carboxylate
• Molecular Formula: C₂₅H₂₇IN₂O₂
• Molecular Weight: 514.40
• CAS Registry Number: 1256584-75-4
• EC Number: 812-677-7
• SMILES: CCC1=C(C=C(C=C1)C(C)(C)C2=C(C3=C(N2)C=C(C=C3)C#N)C(=O)OC(C)(C)C)I

Properties

• Solubility: Insoluble (8.2E^-6 g/L) (25 °C), Calc.^*
• Density: 1.43±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester is a complex organic molecule with a distinctive structure that has attracted attention in the fields of organic synthesis and medicinal chemistry. This compound features an indole core with multiple substituents, including a cyano group, an iodinated phenyl group, and a tert-butyl ester, which contribute to its unique chemical properties and potential applications.

The discovery of 6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester was part of research aimed at developing new molecules with potential therapeutic applications. The indole ring system is known for its presence in many biologically active compounds and its ability to interact with various biological targets. The addition of a cyano group at the 6-position of the indole ring increases the compound's reactivity and can influence its interactions with enzymes and receptors.

The 4-ethyl-3-iodophenyl group attached to the indole core introduces additional functionality. Iodine, a highly reactive halogen, enhances the molecule's ability to undergo cross-coupling reactions, which are valuable in the synthesis of complex organic compounds. The ethyl group adds steric hindrance, influencing the molecule’s interaction with biological targets. The methylethyl substituent on the phenyl ring provides further steric effects and contributes to the molecule's overall stability.

The tert-butyl ester group is another important feature of this compound. Tert-butyl esters are commonly used in organic chemistry as protecting groups for carboxylic acids. They can be easily removed under mild conditions, making them versatile for various synthetic applications. The ester group also helps in improving the solubility of the compound, which is beneficial for its use in biological testing and drug formulation.

One of the primary applications of 6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester is in the development of novel pharmaceuticals. The indole core and cyano group make it a valuable scaffold for designing compounds with potential biological activity. The iodinated phenyl group enables further chemical modifications through cross-coupling reactions, allowing researchers to tailor the molecule's properties for specific therapeutic targets. This approach can lead to the development of new drugs with improved efficacy and selectivity.

The compound also has applications in materials science. Its ability to undergo chemical transformations and form conjugated systems makes it suitable for creating advanced materials with specific electronic or optical properties. For example, it can be used to synthesize organic semiconductors or sensors, leveraging its unique structural features to achieve desired material characteristics.

The synthesis of 6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester involves several steps, including the introduction of the cyano group and the iodinated phenyl ring. The tert-butyl ester is typically added through esterification reactions, which provide a stable protecting group that can be removed when needed.

In summary, 6-Cyano-2-[1-(4-ethyl-3-iodophenyl)-1-methylethyl]-1H-indole-3-carboxylic acid 1,1-dimethylethyl ester is a valuable compound in organic synthesis and materials science. Its unique structure and functional groups offer opportunities for developing new pharmaceuticals and advanced materials with specific properties. Ongoing research and exploration of this compound are expected to reveal further applications and benefits.

References

2016. Alectinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0212