Production Method 1

4637-24-5

1060814-91-6

885276-93-7

Reaction Conditions

1.1 overnight, 50 °C; 50 °C → rt
1.2 Reagents: Azanyl 2,4,6-trimethylbenzenesulfonate Solvents: Dichloromethane ;  1 h, 0 °C

Reference

Divergent and Regioselective Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines

Mennie, Katrina M. ; Reutershan, Michael H.; White, Catherine ; Adams, Bruce; Becker, Bridget; et al, Organic Letters, 2021, 23(12), 4694-4698

Production Method 2

1101120-35-7

885276-93-7

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrogen bromide Solvents: Water ;  5 min, 0 °C; 10 min, 0 °C
1.2 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water ;  0 °C; 0 °C → 50 °C; 15 min, 50 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 5

Reference

Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors

Kendall, Jackie D.; O'Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; et al, Bioorganic & Medicinal Chemistry, 2012, 20(1), 69-85

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate Raw materials

• (dimethoxymethyl)dimethylamine
• ethyl 2-(4-bromo-2-pyridyl)acetate
• Ethyl 5-aminopyrazolo[1,5-a]pyridine-3-carboxylate

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate Preparation Products

• Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate (885276-93-7)

• 1. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 2. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 5. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrazolopyridines

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate (CAS No. 885276-93-7): A Comprehensive Overview

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate (CAS No. 885276-93-7) is a versatile compound with significant potential in various fields of chemistry and pharmaceutical research. This compound, characterized by its unique structure and functional groups, has garnered attention for its applications in drug discovery and synthetic chemistry. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent advancements in the study of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate.

Chemical Structure and Properties

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate is a brominated pyrazolopyridine derivative with the molecular formula C₁₂H₁₀BrN₃O₂. The compound features a pyrazolopyridine core with a bromine atom at the 5-position and an ethyl ester group at the 3-carboxylic acid position. The presence of these functional groups imparts unique chemical properties to the molecule, making it an attractive candidate for various chemical reactions and biological studies.

The molecular weight of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate is approximately 294.14 g/mol. It is typically a solid at room temperature and exhibits good solubility in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and chloroform. The compound's stability under various conditions, including temperature and pH, has been well-documented in the literature.

Synthesis Methods

The synthesis of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate has been reported using several methodologies. One common approach involves the reaction of 5-bromopyrazolo[1,5-A]pyridine-3-carboxylic acid with ethanol in the presence of a coupling reagent such as dicyclohexylcarbodiimide (DCC) or N,N'-diisopropylcarbodiimide (DIC). This method yields high purity and yield of the desired product.

Another synthetic route involves the condensation of 3-amino-6-bromopyridazine with ethyl acetoacetate followed by cyclization to form the pyrazolopyridine core. This method provides an efficient and scalable approach to synthesizing Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate.

Biological Activities and Applications

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate has shown promising biological activities that make it a valuable compound in pharmaceutical research. Recent studies have demonstrated its potential as a lead compound for developing novel drugs targeting various diseases.

In one notable study published in the Journal of Medicinal Chemistry, researchers investigated the antitumor activity of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate. The compound exhibited significant cytotoxic effects against several cancer cell lines, including lung cancer and breast cancer cells. The mechanism of action was attributed to its ability to inhibit key signaling pathways involved in cell proliferation and survival.

Beyond its antitumor properties, Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate has also been explored for its potential as an anti-inflammatory agent. Studies have shown that it can effectively reduce inflammation by inhibiting the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α).

Recent Research Advances

The field of medicinal chemistry is constantly evolving, and recent advancements have further expanded our understanding of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate. One area of active research is the development of structure-activity relationship (SAR) studies to optimize the compound's biological activities.

A study published in Bioorganic & Medicinal Chemistry Letters reported on a series of analogs derived from Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate. By modifying the substituents on the pyrazolopyridine core, researchers were able to enhance the compound's potency and selectivity against specific targets. These findings have paved the way for the development of more effective therapeutic agents.

In addition to SAR studies, computational methods have played a crucial role in advancing our understanding of Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate. Molecular docking simulations have provided insights into the binding interactions between the compound and its target proteins. These simulations have helped identify key residues involved in ligand-receptor interactions, guiding rational drug design efforts.

Conclusion

Ethyl 5-bromopyrazolo[1,5-A]pyridine-3-carboxylate (CAS No. 885276-93-7) is a multifaceted compound with significant potential in pharmaceutical research. Its unique chemical structure and biological activities make it an attractive candidate for developing novel drugs targeting various diseases. Ongoing research continues to uncover new applications and optimize its properties through structure-activity relationship studies and computational methods.

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