4-bromo-5-methoxy-1H-pyrrolo[2,3-c]pyridine
[CAS# 1254163-78-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 4-bromo-5-methoxy-1H-pyrrolo[2,3-c]pyridine
• Molecular Formula: C₈H₇BrN₂O
• Molecular Weight: 227.06
• CAS Registry Number: 1254163-78-4
• EC Number: 833-705-4
• SMILES: COC1=NC=C2C(=C1Br)C=CN2

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 339.5±37.0 ºC 760 mmHg (Calc.)^*
• Flash point: 159.1±26.5 ºC (Calc.)^*
• Index of refraction: 1.678 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

4-Bromo-5-methoxy-1H-pyrrolo\[2,3-c]pyridine is a heterocyclic aromatic compound that belongs to the pyrrolopyridine class, which is of significant interest in medicinal and synthetic organic chemistry. The structure of this molecule incorporates a fused bicyclic system composed of a pyrrole ring and a pyridine ring, substituted with a bromine atom at the 4-position and a methoxy group at the 5-position. This specific substitution pattern imparts distinctive electronic and steric properties to the molecule, making it a versatile intermediate for further chemical transformations and potential bioactive molecule development.

The compound is primarily utilized as a synthetic building block in pharmaceutical research, particularly in the design and development of kinase inhibitors and other biologically active small molecules. Its core scaffold, the pyrrolo\[2,3-c]pyridine system, is found in various biologically active compounds, including some that modulate protein kinases, which are enzymes involved in regulating essential cellular processes such as growth, differentiation, and apoptosis. Because of its structural resemblance to purine, a key component of nucleotides, the pyrrolopyridine moiety often serves as a privileged scaffold in drug discovery.

4-Bromo-5-methoxy-1H-pyrrolo\[2,3-c]pyridine is most commonly employed in the context of palladium-catalyzed cross-coupling reactions such as Suzuki, Buchwald-Hartwig, and Sonogashira couplings. The bromine substituent at the 4-position enables facile functionalization, allowing the introduction of a wide range of aryl, heteroaryl, alkynyl, or amino groups. The methoxy group at the 5-position serves both as an electron-donating substituent and as a potential handle for further derivatization, such as demethylation or substitution with other functional groups.

In the synthetic route toward kinase inhibitors, 4-bromo-5-methoxy-1H-pyrrolo\[2,3-c]pyridine has been used as a key intermediate in constructing libraries of analogs with varying pharmacological profiles. Compounds derived from this core structure have been evaluated for anticancer, anti-inflammatory, and antiviral activities. In particular, the 4-bromo substituent allows for diversification of the molecule through metal-catalyzed bond formation reactions, enabling rapid generation of chemical diversity that is critical in lead optimization studies.

The compound has also been included in synthetic schemes aimed at producing fluorescent molecules, ligands for molecular probes, and molecules with potential CNS (central nervous system) activity. The electron-rich nature of the methoxy group can influence the reactivity of the heterocycle and modulate the binding characteristics of derivatives in biological systems.

Commercially, 4-bromo-5-methoxy-1H-pyrrolo\[2,3-c]pyridine is available through various chemical suppliers, typically in research-grade purity. It is handled using standard procedures appropriate for laboratory reagents, with general recommendations to avoid exposure to moisture and light to maintain stability. There is no known pharmacological application of this compound itself in humans, and it has not been approved as a therapeutic agent. Its use remains confined to preclinical research and chemical synthesis.

Overall, 4-bromo-5-methoxy-1H-pyrrolo\[2,3-c]pyridine exemplifies a class of synthetically valuable heterocycles that serve as foundational elements in the construction of more complex and potentially bioactive molecules within medicinal chemistry and pharmaceutical research.