4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine
[CAS# 425380-37-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Bromopyridine
• Name: 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine
• Molecular Formula: C₈H₇BrN₂O
• Molecular Weight: 227.06
• CAS Registry Number: 425380-37-6
• EC Number: 846-389-8
• SMILES: COC1=NC=C(C2=C1NC=C2)Br

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 347.0±37.0 ºC 760 mmHg (Calc.)^*
• Flash point: 163.6±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: H303-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P301+P317-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
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	5	H303
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

4-Bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine is a heteroaromatic compound that belongs to the fused pyrrolopyridine family. Its core structure consists of a pyridine ring fused to a pyrrole moiety, with a bromine atom at the 4-position and a methoxy group at the 7-position. The presence of multiple functional groups and nitrogen atoms within a condensed ring system makes it synthetically versatile and a useful intermediate in medicinal chemistry.

The pyrrolo[2,3-c]pyridine scaffold is recognized for its presence in various biologically active molecules, particularly those targeting protein kinases, G-protein coupled receptors, and other enzyme classes. The bromine substituent on the aromatic ring allows for further functionalization through metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura, Buchwald-Hartwig, or Sonogashira couplings. This functional handle enables the rapid derivatization of the compound, allowing researchers to build more complex structures for pharmacological screening.

The methoxy group at the 7-position contributes to the molecule’s electronic and steric properties. Electron-donating groups such as methoxy can influence the reactivity of the adjacent positions on the ring system and affect binding interactions in biological targets through π-stacking or hydrogen-bond acceptor capabilities.

Applications of 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine are mainly found in the field of drug discovery. Analogous compounds featuring this heterocycle have been reported in the development of kinase inhibitors, including those aimed at oncogenic targets such as ALK, EGFR, and BTK. The rigid planar structure and hydrogen-bonding potential of the fused ring system allow for strong interactions within enzyme active sites or receptor binding pockets.

In synthetic chemistry, this compound serves as a key intermediate. Its brominated position is especially valuable in diversity-oriented synthesis strategies, allowing rapid construction of libraries of substituted pyrrolo[2,3-c]pyridine derivatives. The methoxy group also provides opportunities for further derivatization via demethylation or conversion into other functional groups.

Overall, 4-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine is a structurally rich and synthetically flexible compound, with well-established use as a building block in pharmaceutical research and heterocyclic chemistry. Its presence in the synthesis of biologically relevant molecules highlights its importance in the early stages of drug design and chemical biology.

References

2016. From ortho-Substituted Nitropyridines (Bartoli Synthesis). Science of Synthesis, 1.
URL: https://www.thieme.de/en/thieme-chemistry/science-of-synthesis-54713.htm

2020. Synthesis of ABBV-744. Synfacts, 16(9).
DOI: 10.1055/s-0040-1707095