Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate NEW

1.Structural Breakdown (What the Name Means

This is a complex organic molecule, and its systematic name describes its structure piece-by-piece:

• Ethyl ... carboxylate: This indicates an ester functional group (-COOCH₂CH₃) attached to the core structure. This makes the molecule relatively lipophilic (fat-soluble).

• 6-Bromo: A bromine atom (Br) is attached to carbon #6 on the indole ring.

• 5-Hydroxy: A hydroxyl group (-OH) is attached to carbon #5. This group can act as a hydrogen bond donor and acceptor.

• 1-Methyl: A methyl group (-CH₃) is attached to the nitrogen atom (N) of the indole ring. This "protects" the nitrogen and alters its electronic properties.

• 2-[(Phenylsulfanyl)methyl]: A thiobenzyl ether group (-CH₂-S-C₆H₅) is attached to carbon #2 of the indole ring. The sulfur atom provides potential for further oxidation or metal coordination.

• Indole: The core of the molecule is an indole ring system—a fundamental structure in organic chemistry consisting of a benzene ring fused to a pyrrole ring. Indoles are found in many natural products (e.g., tryptophan, serotonin) and pharmaceuticals.

2. Key Properties and Characteristics

• Molecular Weight: Relatively high (~434 g/mol), typical for a synthetic intermediate.

• Solubility: Likely soluble in organic solvents like dichloromethane, ethyl acetate, and dimethylformamide (DMF) due to its lipophilic ester and aromatic groups. The phenolic -OH group may grant slight solubility in basic aqueous solutions.

• Reactivity: The molecule contains multiple sites for further chemical manipulation:

• The bromine atom is an excellent handle for metal-catalyzed cross-coupling reactions (e.g., Suzuki, Heck reactions) to attach more complex groups.

  The phenolic -OH group can be alkylated, acylated, or used to form ethers.

  The ester can be hydrolyzed to a carboxylic acid or reduced to an alcohol.

  The sulfide (thioether) can be oxidized to a sulfoxide or sulfone.

3. Synthesis and Role

This compound is not a naturally occurring substance and is not a final product like a drug or material.

• It is a Synthetic Intermediate: This molecule is almost exclusively a key building block synthesized in a laboratory for use in organic and medicinal chemistry research.

• Purpose: Its complex, multi-functional structure is carefully constructed to serve as a precursor for the synthesis of more elaborate target molecules. A chemist would use its reactive sites (Br, OH) to build a larger, more complex structure around the indole core.

4. Potential Applications and Uses

Given its structure, it is designed for advanced synthetic applications, likely in:

• Medicinal Chemistry Research: The indole core is a "privileged scaffold" in drug discovery. This specific molecule could be used to synthesize novel potential pharmaceuticals targeting a wide range of diseases, particularly in:

• Oncology: Kinase inhibitors or apoptosis inducers.

  Neurology: Serotonin receptor modulators.

• Materials Science: As a building block for creating organic ligands that could coordinate with metals to form catalysts or functional materials.

• Chemical Biology: As a probe to study biological systems or enzyme mechanisms.

Summary

In essence, Ethyl 6-bromo-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate is a sophisticated, multi-functional synthetic intermediate. Its value lies not in what it is, but in what it can become. A chemist designed it with specific reactive handles (Br, OH, ester, sulfide) to allow for systematic and precise chemical transformations en route to creating a target molecule for research, most likely in the field of drug discovery.