4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine: Key Facts & FAQs
4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine: Key Facts & FAQs
4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine is a halogenated 7-azaindole-based heterocyclic compound widely used as a synthetic building block in medicinal chemistry and kinase-inhibitor drug discovery programs.
- Product Name
- 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine
- SKU
- C177188
- Core Scaffold
- 7-Azaindole (pyrrolo[2,3-b]pyridine)
- Key Functional Groups
- C-4 chloro substituent; C-3 methyl substituent; NH pyrrole
- Primary Use
- Synthetic intermediate and building block for heterocyclic drug candidates
- Supplier SKU (Aladdin)
- C177188
What Is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine?
4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine is a bicyclic heterocyclic compound belonging to the pyrrolopyridine family. Its core structure, the pyrrolo[2,3-b]pyridine (7-azaindole) scaffold, consists of a pyrrole ring fused to a pyridine ring at the [2,3-b] bond junction. The compound bears a chlorine atom at the 4-position and a methyl group at the 3-position of the fused ring system, with a free NH on the pyrrole nitrogen.
The electron-deficient nature of the pyridine nitrogen and the reactive C-4 chloride make this scaffold particularly attractive as a versatile intermediate in pharmaceutical synthesis. The C-4 chloro group is amenable to nucleophilic aromatic substitution (SNAr) and transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig), enabling rapid diversification of the core for structure-activity relationship (SAR) studies.
Research Applications and Significance
The pyrrolo[2,3-b]pyridine scaffold is a privileged structure in medicinal chemistry, appearing in numerous kinase inhibitor programs. The 7-azaindole motif is known to mimic the adenine moiety of ATP, enabling tight binding within kinase ATP-binding pockets. Compounds derived from 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine have been explored as starting materials or intermediates for inhibitors targeting various protein kinases involved in oncology and inflammatory diseases.
Beyond kinase research, this building block is employed in the synthesis of diverse bioactive heterocycles, including antiviral and antimicrobial candidates. Its dual handles for functionalization — the electrophilic C-4 position and the nucleophilic NH — provide chemists with significant flexibility for library construction and lead optimization.
Handling, Storage, and Safety
As with most halogenated heterocyclic intermediates, 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine should be handled with standard laboratory precautions. Personal protective equipment (PPE) including gloves, lab coat, and eye protection is recommended. Operations generating dust or aerosols should be performed in a well-ventilated fume hood.
The compound 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. It is advisable to keep the container tightly sealed when not in use. Researchers should consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU C177188) for authoritative hazard classifications, first-aid measures, and disposal guidance before use.
Ordering and Availability from Aladdin Scientific
4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine is available from Aladdin Scientific under SKU C177188. Researchers and procurement teams can place orders directly through the Aladdin Scientific website or by contacting the sales team. Multiple pack sizes may be available to suit both small-scale discovery work and larger preparative needs — please check the current product page for up-to-date stock status, pricing, and purity specifications.
For questions about custom quantities, purity certificates (CoA), or technical specifications, contact Aladdin Scientific customer support. Bulk pricing and institutional account options may also be available upon request.
Frequently asked questions
What is 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine used for in research?
It is primarily used as a synthetic building block and intermediate in medicinal chemistry, particularly for the preparation of kinase inhibitor candidates. The reactive C-4 chloro group allows efficient derivatization via cross-coupling or nucleophilic substitution reactions, facilitating the exploration of structure-activity relationships around the 7-azaindole scaffold.
What reactions can be performed at the C-4 chloro position of this compound?
The C-4 chloro substituent is well-suited for palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura (with boronic acids), Buchwald-Hartwig amination, and Negishi coupling, as well as nucleophilic aromatic substitution (SNAr) with amines or other nucleophiles under appropriate conditions. These transformations enable rapid diversification of the pyrrolopyridine core.
How should 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (C177188) be stored?
The compound should be stored in a cool, dry, and well-ventilated area with the container tightly sealed to protect it from moisture and heat. Always consult the product's Safety Data Sheet (SDS) available from Aladdin Scientific for specific storage temperature recommendations and full hazard information.
Is the NH group on the pyrrole ring available for further functionalization?
Yes, the free NH on the pyrrole nitrogen can be protected or alkylated to install N-substituents, providing an additional handle for diversification. Common N-protection strategies include N-sulfonylation or N-alkylation, depending on the downstream synthetic requirements.
Where can I purchase 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine?
This compound is available from Aladdin Scientific under SKU C177188. You can place an order through the Aladdin Scientific website or contact the customer service team for information on pricing, available pack sizes, and current stock. A Certificate of Analysis (CoA) is available upon request.
References
- Aladdin Scientific product page: 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, SKU C177188.
- General reference: 7-azaindole scaffold in kinase inhibitor design — textbook-level medicinal chemistry knowledge. Specific literature citations not provided in source material.
- Cross-coupling reactions of halogenated heterocycles — general synthetic chemistry knowledge. Specific literature 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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