Ethyl 7-Chloroimidazo[1,2-a]pyridine-3-Carboxylate FAQs
Ethyl 7-Chloroimidazo[1,2-a]pyridine-3-Carboxylate FAQs
Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate is a halogenated bicyclic heterocyclic ester that serves as a versatile synthetic building block in medicinal chemistry and drug discovery research.
- Product SKU
- E734636
- Chemical Name
- Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate
- Core Scaffold
- Imidazo[1,2-a]pyridine bicyclic ring system
- Key Functional Groups
- C-7 chloro substituent, C-3 ethyl ester
- Primary Application
- Heterocyclic synthesis, medicinal chemistry intermediate
- Supplier
- Aladdin Scientific
What Is Ethyl 7-Chloroimidazo[1,2-a]pyridine-3-Carboxylate?
Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate (SKU: E734636) is an organic compound featuring a fused bicyclic imidazo[1,2-a]pyridine core. The imidazo[1,2-a]pyridine scaffold consists of an imidazole ring fused to a pyridine ring via the nitrogen atom at position 1 of imidazole and position 2 of pyridine. This compound carries a chlorine atom at the 7-position of the pyridine ring and an ethyl ester functionality at the 3-position of the imidazole ring.
The presence of both the electron-withdrawing chloro substituent and the ester group makes this compound a highly reactive and functionalizable intermediate. It is widely used as a building block in the synthesis of more complex heterocyclic structures relevant to pharmaceutical and agrochemical research.
Chemical Properties and Handling
The imidazo[1,2-a]pyridine core is an aromatic heterocyclic system with notable thermal and chemical stability under standard laboratory conditions. The ethyl ester at the 3-position can undergo hydrolysis under acidic or basic aqueous conditions, yielding the corresponding carboxylic acid, which may be useful as a further synthetic handle.
The 7-chloro substituent is amenable to a range of transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings, enabling efficient diversification of the core scaffold. Researchers should handle this compound using standard laboratory personal protective equipment (PPE), including gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood is recommended. Consult the Safety Data Sheet (SDS) before use.
Storage and Stability Recommendations
For optimal long-term stability, Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate should be stored in a cool, dry, and well-ventilated location, away from moisture, heat, and incompatible materials such as strong oxidizers and strong bases. Sealing the container tightly after each use helps prevent moisture ingress and potential hydrolysis of the ester functionality.
It is good laboratory practice to aliquot the compound into smaller portions to minimize freeze-thaw cycles and repeated exposure to ambient conditions. Always verify current storage recommendations on the product label or Certificate of Analysis (CoA) provided with your shipment from Aladdin Scientific.
Applications in Medicinal Chemistry and Drug Discovery
The imidazo[1,2-a]pyridine scaffold is a privileged structure in medicinal chemistry, appearing in numerous biologically active compounds and approved pharmaceuticals. The scaffold exhibits a range of pharmacological activities in the literature, including kinase inhibition, antimicrobial activity, and central nervous system (CNS) modulation, making it a highly attractive template for drug discovery programs.
Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate is particularly valuable as a versatile intermediate because both the C-7 chloro group and the C-3 ester provide orthogonal handles for further chemical elaboration. This allows medicinal chemists to rapidly generate libraries of analogs for structure–activity relationship (SAR) studies. It is suitable for use in parallel synthesis workflows and high-throughput screening compound preparation.
Ordering, Purity, and Quality Assurance
Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate is available from Aladdin Scientific under SKU E734636. Each lot is accompanied by a Certificate of Analysis (CoA) that documents purity and analytical characterization data. Researchers are encouraged to request the CoA for their specific lot number prior to use to confirm that the material meets the requirements of their application.
For bulk quantities, custom packaging, or specific purity grades, please contact Aladdin Scientific's technical sales team. Orders can be placed through the Aladdin Scientific website or through authorized distributors. For questions regarding shipping, returns, or payment, please refer to Aladdin Scientific's customer service resources or the relevant FAQ sections on the website.
Frequently asked questions
What is the chemical structure of Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate?
The compound features a fused bicyclic imidazo[1,2-a]pyridine ring system, in which an imidazole ring is fused to a pyridine ring through a shared nitrogen. A chlorine atom is located at the 7-position of the pyridine ring, and an ethyl ester group is attached at the 3-position of the imidazole ring.
How should Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate be stored to maintain stability?
Store the compound in a cool, dry, and well-ventilated area, tightly sealed and away from moisture, heat, and strong oxidizing or basic agents. Aliquoting into smaller portions minimizes repeated exposure to ambient conditions. Always refer to the Certificate of Analysis and product label for lot-specific storage instructions.
What reactions can be performed using the 7-chloro group in this compound?
The 7-chloro substituent on the pyridine ring is well-suited for transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura (boronic acid coupling), Buchwald–Hartwig (amination), and Negishi (organozinc) couplings. These reactions enable the introduction of diverse aryl, heteroaryl, amino, or alkyl groups at the 7-position, facilitating analog synthesis for SAR studies.
Is this compound suitable for high-throughput screening library synthesis?
Yes. The orthogonal reactivity of the C-7 chloro group and the C-3 ethyl ester makes Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate an excellent building block for parallel and combinatorial synthesis workflows aimed at generating compound libraries for high-throughput screening (HTS) in drug discovery.
How can I obtain a Certificate of Analysis (CoA) for my lot of E734636?
A Certificate of Analysis is provided with each shipment of E734636 from Aladdin Scientific. You can also request a lot-specific CoA by contacting Aladdin Scientific customer service with your lot number, or by searching for it on the Aladdin Scientific website using your order or lot information.
What personal protective equipment (PPE) is recommended when handling this compound?
Standard laboratory PPE is recommended, including chemical-resistant gloves, safety glasses or goggles, and a lab coat. Handle the compound in a well-ventilated area or fume hood. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before handling for complete hazard and first-aid information.
References
- Aladdin Scientific product page for Ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate, SKU E734636.
- General reference on imidazo[1,2-a]pyridine as a privileged scaffold in medicinal chemistry. Textbook-level knowledge; specific literature citation to be confirmed.
- General reference on Suzuki–Miyaura, Buchwald–Hartwig, and Negishi cross-coupling reactions applicable to aryl chloride substrates. Textbook-level knowledge; specific literature citation to be confirmed.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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