5-Bromo-1h-pyrrolo[2,3-c]pyridine

5-Bromo-1H-pyrrolo[2,3-c]pyridine (CAS 1215387-58-8) is a strategically brominated fused bicyclic scaffold engineered for kinase inhibitor development and heterocyclic diversification in medicinal chemistry. This molecule integrates a pyrrolo[2,3-c]pyridine core—a nitrogen-rich 7-azaindole isostere—with a bromine substituent at the C5 position. The fused 5,6-bicyclic system provides a planar, rigid architecture ideal for π-stacking interactions in ATP-binding pockets, while the C5-bromo handle enables efficient Pd-catalyzed cross-coupling (Suzuki, Buchwald-Hartwig, Sonogashira) to introduce diverse aryl, heteroaryl, or amine substituents. Distinct from the more common pyrrolo[2,3-b]pyridine (7-azaindole) isomers, the [2,3-c] fusion pattern alters the electronic distribution and hydrogen-bonding geometry, offering unique selectivity profiles against kinase targets. This intermediate is particularly valuable for constructing targeted oncology therapeutics, CNS-penetrant scaffolds, and agrochemical actives where fused nitrogen heterocycles enhance metabolic stability and binding affinity. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to azaindole-like architectures with precise nitrogen positioning.

Property

Product Name	5-Bromo-1H-pyrrolo[2,3-c]pyridine
CAS Number	1215387-58-8
Chinese Name	5-溴 -1H-吡咯并 [2,3-c] 吡啶
Synonyms	5-Bromo-1H-pyrrolo[2,3-c]pyridine; 1H-Pyrrolo[2,3-c]pyridine, 5-bromo-; C₇H₅BrN₂ fused heterocycle
Chinese Synonyms	5-溴吡咯并吡啶; 5-溴 -1H-吡咯并 [2,3-c] 吡啶; 溴代氮杂吲哚类似物
Molecular Formula	C₇H₅BrN₂
Molecular Weight	197.03 g/mol
Purity	≥ 98% (HPLC/GC area normalization)
Product Category	Pharmaceutical Intermediates / Fused Heterocycles / Brominated Azaindoles
Appearance	Light brown to brown solid
Melting Point	~240-250°C (estimated, decomposition possible, literature reference recommended)
Storage Conditions	Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong bases to avoid debromination or ring degradation.
Shelf Life	24 months under recommended storage conditions
Packaging	customized according to customer requirements
Applications	Kinase inhibitor synthesis (ATP-mimetic scaffolds), oncology drug development, CNS-penetrant scaffold design, agrochemical active ingredient precursors, heterocyclic library synthesis via C5 coupling
Reactivity	Suitable for Suzuki coupling, Buchwald-Hartwig amination, Sonogashira coupling (C5-Br displacement), N1-alkylation/acylation, electrophilic aromatic substitution at C3/C4, and metal-catalyzed C–H functionalization
Special Note	Fused Bicyclic Scaffold—distinct electronic profile vs. pyrrolo[2,3-b]pyridine (7-azaindole) isomers. The C5-Br position offers strategic diversification. Part of our fused nitrogen heterocycle series.