6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine: Properties & Uses
6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine: Properties & Uses
6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine is a brominated, N-alkylated bicyclic heterocycle that serves as a versatile synthetic building block in medicinal chemistry and drug discovery research.
- Product Name
- 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine
- SKU
- B178924
- Core Scaffold
- Imidazo[4,5-b]pyridine (fused bicyclic: imidazole ring fused to pyridine)
- Key Functional Groups
- C6-bromo substituent (electrophilic cross-coupling handle); N3-ethyl group (N-alkylation)
- Primary Research Use
- Synthetic intermediate for medicinal chemistry and drug discovery programs
- Supplier
- Aladdin Scientific
Chemical Structure and Key Structural Features
6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine belongs to the imidazo[4,5-b]pyridine family of fused bicyclic heteroaromatics. The parent scaffold consists of an imidazole ring fused to a pyridine ring at the [4,5-b] positions, creating a planar, electron-deficient aromatic system that is widely recognized in medicinal chemistry for its favorable drug-like properties.
Two key substitutions define this compound: (1) a bromine atom at the C6 position of the pyridine ring, which serves as an activated electrophilic handle for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings; and (2) an ethyl group on the N3 nitrogen of the imidazole ring, which locks the tautomeric equilibrium present in the unsubstituted parent scaffold and fine-tunes the lipophilicity and metabolic profile of downstream derivatives.
The combination of a reactive C–Br bond and a fixed N-alkyl group makes this molecule a bifunctional building block suitable for both C–C and C–heteroatom bond-forming transformations in multi-step synthetic sequences.
Role as a Synthetic Building Block in Drug Discovery
Imidazo[4,5-b]pyridine derivatives are well-established privileged scaffolds in drug discovery. The bicyclic heteroaromatic core is found in a range of bioactive molecules, particularly those targeting protein kinases, where the scaffold can act as a hinge-binding pharmacophore mimicking adenine in the ATP binding site.
The C6-bromo substituent of 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine enables straightforward diversification via transition-metal-catalyzed coupling reactions, allowing medicinal chemists to efficiently install aryl, heteroaryl, amino, or alkynyl groups at that position. This synthetic versatility accelerates structure–activity relationship (SAR) exploration during lead optimization campaigns.
The N3-ethyl group prevents N1/N3 tautomerism, ensuring consistent binding geometry when incorporated into candidate molecules. This regioselective N-alkylation also modifies the electron density of the aromatic system, influencing the potency and selectivity of the resulting pharmacophores. Together, these features make SKU B178924 a practically valuable reagent for assembling focused compound libraries targeting kinases and related enzyme classes.
Handling, Storage, and Laboratory Safety
As with all organobromine heterocyclic intermediates, 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine should be handled in accordance with standard laboratory safety practices. Researchers should consult the product Safety Data Sheet (SDS) prior to use. Personal protective equipment including chemical-resistant gloves, laboratory coat, and safety eyewear is recommended when handling this compound.
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from incompatible materials such as strong oxidizing agents and strong bases. Proper storage conditions help maintain compound integrity and purity over time. Aladdin Scientific recommends referencing the specific storage conditions stated on the product label and certificate of analysis (CoA) supplied with SKU B178924.
Disposal of this compound and any waste solutions should comply with applicable local, national, and institutional regulations governing the disposal of chemical waste.
Ordering and Quality Information
6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine is available from Aladdin Scientific under SKU B178924. Each lot is accompanied by a certificate of analysis (CoA) confirming identity and purity. Researchers requiring specific purity grades, larger quantities, or custom packaging are encouraged to contact Aladdin Scientific's technical and sales team for tailored solutions.
For procurement teams, the product can be ordered directly through the Aladdin Scientific online catalog. Volume pricing and institutional account options may be available; please inquire with your regional Aladdin Scientific representative for details on pricing, promotions, and available stock.
Frequently asked questions
What cross-coupling reactions can be performed using the C6-bromo group of 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine?
The C6-bromo substituent is well-suited for a variety of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (aryl/heteroarylboronic acid coupling), Buchwald–Hartwig (C–N bond formation), Sonogashira (alkyne coupling), and related transition-metal-mediated transformations. These reactions allow rapid introduction of diverse substituents at the C6 position for SAR studies.
Why is N-alkylation at the N3 position important for this imidazopyridine compound?
The imidazo[4,5-b]pyridine parent scaffold can exist as N1-H or N3-H tautomers in solution, which can complicate binding-mode prediction and pharmacological profiling. N-alkylation at N3 with an ethyl group locks the compound into a single, defined regiochemical form, providing consistent electronic properties and a predictable binding geometry in downstream drug candidates. It also modestly increases lipophilicity, which can influence membrane permeability.
What are typical research applications for imidazo[4,5-b]pyridine scaffolds like this compound?
Imidazo[4,5-b]pyridine scaffolds are widely used in medicinal chemistry programs targeting protein kinases, where they can serve as ATP-competitive hinge-binding pharmacophores. They also appear in research directed toward other enzyme classes and receptor targets. Building blocks such as 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine (SKU B178924) are employed to construct focused compound libraries for high-throughput screening and lead optimization.
How should I store SKU B178924 to maintain its purity?
Store 6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine in a tightly sealed container under cool, dry, and well-ventilated conditions, away from strong oxidants and bases. Always refer to the specific storage instructions on the product label and the certificate of analysis (CoA) supplied with each lot. If in doubt, contact Aladdin Scientific for guidance.
References
- General reference: Imidazo[4,5-b]pyridine as a privileged scaffold in medicinal chemistry — textbook-level knowledge; specific primary literature citation not provided in source material.
- General reference: Palladium-catalyzed cross-coupling reactions of aryl and heteroaryl bromides (Suzuki, Buchwald-Hartwig, Sonogashira) — standard synthetic chemistry references; specific citations not provided in source material.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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