4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine
[CAS# 1445993-85-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine
• Molecular Formula: C₁₅H₁₃BrN₂O₃S
• Molecular Weight: 381.24
• CAS Registry Number: 1445993-85-0
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=C2C(=NC=C3Br)OC

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 525.8±60.0 ºC 760 mmHg (Calc.)^*
• Flash point: 271.8±32.9 ºC (Calc.)^*
• Index of refraction: 1.661 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

4-Bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine is a synthetic heterocyclic compound that features a fused pyrrolo[2,3-c]pyridine core substituted with a bromine atom at the 4-position, a methoxy group at the 7-position, and a tosyl (p-toluenesulfonyl) group at the nitrogen atom. This structural motif reflects a combination of electron-donating and electron-withdrawing substituents on a bicyclic nitrogen-containing aromatic system, contributing to its reactivity and usefulness as a synthetic intermediate in medicinal and materials chemistry.

The pyrrolo[2,3-c]pyridine framework is a privileged structure found in many biologically active compounds, due to its structural resemblance to purines and its ability to engage in hydrogen bonding and π–π interactions. The presence of a bromine atom at the 4-position introduces a useful synthetic handle for further functionalization via cross-coupling reactions such as Suzuki–Miyaura, Sonogashira, or Buchwald–Hartwig reactions. These transformations allow for rapid diversification of the molecular scaffold, which is particularly useful in drug discovery and the development of small-molecule libraries.

The methoxy group at the 7-position typically enhances the compound’s electron density and may influence both regioselectivity and reactivity in electrophilic substitution reactions. It can also impact solubility and modulate the electronic properties of the aromatic ring system, affecting binding interactions with biological targets.

The tosyl group on the nitrogen atom serves dual roles: it provides steric protection during synthetic transformations and enhances the compound’s chemical stability. Moreover, N-tosylation prevents unwanted tautomeric equilibria or protonation of the nitrogen, which is particularly important in preserving the desired aromatic structure during multi-step synthesis.

4-Bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine has been employed as a building block in the preparation of complex molecules with potential biological activities. Its brominated position is amenable to derivatization, making it valuable in the design of kinase inhibitors, antiviral agents, and ligands for receptor studies. The compound also serves as a useful precursor in the synthesis of extended polycyclic systems and heteroaromatic frameworks for use in pharmaceutical and agrochemical research.

Overall, this compound represents a functionally rich heterocycle designed for use in modern synthetic chemistry, with well-defined sites for chemical modification and a core structure that is compatible with both chemical and biological applications. Its utility is derived from the combination of reactivity, stability, and pharmacophoric potential inherent to the pyrrolo[2,3-c]pyridine system and its substituents.