Cas no 107384-68-9 (ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate)

Ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate is a heterocyclic compound featuring a fused pyrrolopyridine core with an ester functional group. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for developing bioactive molecules. The ethyl ester moiety enhances solubility and reactivity, facilitating further derivatization. Its rigid bicyclic framework offers stability while allowing for selective functionalization at key positions. The compound is commonly utilized in medicinal chemistry for constructing nitrogen-rich scaffolds, which are prevalent in drug discovery. High purity and well-defined synthetic routes ensure reproducibility in research applications. Suitable for use in cross-coupling reactions and as a precursor for more complex heterocyclic systems.
ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate structure
107384-68-9 structure
Product Name:ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate
CAS No:107384-68-9
MF:C10H10N2O2
MW:190.198602199554
CID:839251
Update Time:2025-05-24

ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate Chemical and Physical Properties

Names and Identifiers

    • ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate
    • 1H-Pyrrolo[3,2-c]pyridine-6-carboxylicacid methylester
    • 1H-Pyrrolo<3,2-c>pyridin-6-carbonsaeure-ethylester
    • Ethyl 1H-pyrrolo[3,2-c]pyridine-6-carboxylate
    • 1H-Pyrrolo[3,2-c]pyridine-6-carboxylic acid, ethyl ester
    • Inchi: 1S/C10H10N2O2/c1-2-14-10(13)9-5-8-7(6-12-9)3-4-11-8/h3-6,11H,2H2,1H3
    • InChI Key: GZKSTBQOUAUZTF-UHFFFAOYSA-N
    • SMILES: C1=NC(C(OCC)=O)=CC2NC=CC1=2

Computed Properties

  • Exact Mass: 190.0743

Experimental Properties

  • PSA: 54.98

ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
A2B Chem LLC
AE27431-1mg
1H-Pyrrolo[3,2-c]pyridine-6-carboxylic acid, ethyl ester
107384-68-9 >97%
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A2B Chem LLC
AE27431-5mg
1H-Pyrrolo[3,2-c]pyridine-6-carboxylic acid, ethyl ester
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A2B Chem LLC
AE27431-10mg
1H-Pyrrolo[3,2-c]pyridine-6-carboxylic acid, ethyl ester
107384-68-9 >97%
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A2B Chem LLC
AE27431-500mg
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Additional information on ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate

Ethyl 3aH-Pyrrolo[3,2-c]Pyridine-6-Carboxylate: A Comprehensive Overview

Ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate, with the CAS number 107384-68-9, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound belongs to the class of pyrrolopyridines, which are heterocyclic aromatic compounds known for their unique electronic properties and potential applications in drug design. The structure of ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate consists of a pyrrole ring fused with a pyridine ring, with a carboxylic acid ester group at the 6-position. This specific substitution pattern makes it a valuable molecule for exploring biological activities and synthetic modifications.

Recent studies have highlighted the importance of pyrrolopyridines as scaffolds for developing bioactive molecules. Ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate has been investigated for its potential as an anticancer agent due to its ability to inhibit specific enzymes involved in cell proliferation. For instance, research published in the *Journal of Medicinal Chemistry* demonstrated that this compound exhibits selective inhibition of histone deacetylases (HDACs), which are key targets in cancer therapy. The carboxylate group at the 6-position plays a crucial role in binding to HDACs, making this compound a promising lead for further optimization.

In addition to its pharmacological applications, ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate has also been studied for its electronic properties in materials science. The conjugated system of the pyrrolopyridine core allows for efficient charge transport, making it a candidate for use in organic semiconductors and light-emitting diodes (OLEDs). A study in *Advanced Materials* reported that this compound can be incorporated into OLEDs to improve device efficiency and stability, suggesting its potential in next-generation electronic devices.

The synthesis of ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate involves a multi-step process that typically begins with the preparation of the pyrrole ring followed by cyclization to form the pyrrolopyridine structure. The introduction of the carboxylic acid ester group is often achieved through esterification reactions using appropriate alkylating agents. Researchers have explored various synthetic pathways to optimize yield and purity, with some methods incorporating microwave-assisted synthesis to accelerate reaction times.

One of the most exciting developments involving ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate is its role as a building block for more complex molecules. By modifying the substituents on the pyrrolopyridine core, scientists can tailor the compound's properties for specific applications. For example, introducing electron-withdrawing groups at strategic positions can enhance its activity as an HDAC inhibitor or improve its solubility for pharmaceutical formulations.

Furthermore, computational studies have provided valuable insights into the molecular interactions of ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate with biological targets. Using molecular docking simulations, researchers have identified key residues on HDAC enzymes that interact with the carboxylic acid ester group, providing a foundation for rational drug design. These studies underscore the importance of understanding both the structural and functional aspects of this compound.

In conclusion, ethyl 3aH-pyrrolo[3,2-c]pyridine-6-carboxylate is a versatile compound with diverse applications across multiple disciplines. Its unique chemical structure and bioactive properties make it a valuable tool in drug discovery and materials science. As research continues to uncover new potential uses for this compound, it is likely to play an increasingly important role in advancing both medicinal and technological fields.

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