Production Method 1

271-63-6

55052-28-3

55052-27-2

80235-01-4

Reaction Conditions

1.1 Solvents: Ethyl acetate ;  < 20 °C; 2 h, 25 °C
2.1 Reagents: Tripotassium phosphate Solvents: Water ;  pH 10, 10 - 15 °C; 1 h, 0 °C
3.1 Reagents: Methanesulfonyl chloride Solvents: Dimethylformamide ;  1 h, 60 - 75 °C; 5 h, 70 °C; 70 °C → 40 °C
3.2 Solvents: Water ;  < 15 °C
3.3 Reagents: Sodium hydroxide Solvents: Water ;  0.5 h, 10 °C

Reference

Highly Regioselective and Practical Synthesis of 5-Bromo-4-chloro-3-nitro-7-azaindole

Han, Chong ; et al, Organic Process Research & Development, 2017, 21(4), 664-668

Production Method 2

55052-24-9

55052-28-3

55052-27-2

80235-01-4

Reaction Conditions

1.1 Reagents: Methanesulfonyl chloride Solvents: Dimethylformamide ;  1 h, 60 - 75 °C; 5 h, 70 °C; 70 °C → 40 °C
1.2 Solvents: Water ;  < 15 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  0.5 h, 10 °C

Reference

Highly Regioselective and Practical Synthesis of 5-Bromo-4-chloro-3-nitro-7-azaindole

Han, Chong ; et al, Organic Process Research & Development, 2017, 21(4), 664-668

Production Method 3

16887-60-8

504440-63-5

55052-28-3

55052-27-2

80235-01-4

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Solvents: Water ;  pH 10, 10 - 15 °C; 1 h, 0 °C
2.1 Reagents: Methanesulfonyl chloride Solvents: Dimethylformamide ;  1 h, 60 - 75 °C; 5 h, 70 °C; 70 °C → 40 °C
2.2 Solvents: Water ;  < 15 °C
2.3 Reagents: Sodium hydroxide Solvents: Water ;  0.5 h, 10 °C

Reference

Highly Regioselective and Practical Synthesis of 5-Bromo-4-chloro-3-nitro-7-azaindole

Han, Chong ; et al, Organic Process Research & Development, 2017, 21(4), 664-668

4-Chloro-1H-pyrrolo[2,3-b]pyridine Raw materials

• 3-Chlorobenzoate
• 1H-pyrrolo[2,3-b]pyridine
• 1H-pyrrolo(2,3-b)pyridine 7-oxide
• 7-oxido-1H-pyrrolo[2,3-b]pyridin-7-ium

4-Chloro-1H-pyrrolo[2,3-b]pyridine Preparation Products

• 6-Chloro-1H-pyrrolo[2,3-B]pyridine (55052-27-2)
• 3-chloro-1H-pyrrolo[2,3-b]pyridine (80235-01-4)
• 4-Chloro-1H-pyrrolo[2,3-b]pyridine (55052-28-3)

• 1. Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200
  Shanshan Liu,Heng Yang,Lin-Yu Jiao,Jian-Hua Zhang,Chen Zhao,Yangmin Ma,Xiufang Yang Org. Biomol. Chem. 2019 17 10073
• 2. Topological features and electronic structure of 4-chloro-1H-pyrrolo[2,3-b]pyridine: experimental charge density analysis and DFT studies
  Dipak K. Hazra,Alok K. Mukherjee,Madeleine Helliwell,Monika Mukherjee CrystEngComm 2012 14 993
• 3. Recent advances in the global ring functionalization of 7-azaindoles
  Prakash Kannaboina,Krishanu Mondal,Joydev K. Laha,Parthasarathi Das Chem. Commun. 2020 56 11749
• 4. Catalyst and additive-free regioselective oxidative C–H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN
  Chengtao Feng,Ya Peng,Guangrong Ding,Xiangxiao Li,Chang Cui,Yizhe Yan Chem. Commun. 2018 54 13367
• 5. Organometallic methods for the synthesis and functionalization of azaindoles
  Jinhua J. Song,Jonathan T. Reeves,Fabrice Gallou,Zhulin Tan,Nathan K. Yee,Chris H. Senanayake Chem. Soc. Rev. 2007 36 1120

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

Recent Advances in the Research of 4-Chloro-1H-pyrrolo[2,3-b]pyridine (CAS: 55052-28-3)

4-Chloro-1H-pyrrolo[2,3-b]pyridine (CAS: 55052-28-3) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. This compound serves as a key intermediate in the synthesis of various biologically active molecules, particularly in the design of kinase inhibitors and other therapeutic agents. Recent studies have explored its potential in targeting specific pathways involved in cancer, inflammation, and infectious diseases.

A recent study published in the Journal of Medicinal Chemistry (2023) highlighted the role of 4-Chloro-1H-pyrrolo[2,3-b]pyridine as a scaffold for developing selective JAK2 inhibitors. The researchers demonstrated that modifications at the 4-position of the pyrrolopyridine core significantly influenced the compound's binding affinity and selectivity towards JAK2, a kinase implicated in myeloproliferative disorders. The study utilized molecular docking and in vitro assays to validate the compound's efficacy, paving the way for further optimization.

Another notable advancement was reported in Bioorganic & Medicinal Chemistry Letters (2024), where 4-Chloro-1H-pyrrolo[2,3-b]pyridine was employed as a precursor for synthesizing novel antiviral agents. The research team synthesized a series of derivatives and evaluated their activity against SARS-CoV-2. One derivative, featuring a trifluoromethyl group at the 5-position, exhibited promising inhibitory effects on viral replication, suggesting its potential as a lead compound for COVID-19 therapeutics.

In addition to its therapeutic applications, 4-Chloro-1H-pyrrolo[2,3-b]pyridine has also been investigated for its role in chemical biology tools. A study in ACS Chemical Biology (2023) described its use in developing fluorescent probes for detecting reactive oxygen species (ROS) in live cells. The probe, designed by conjugating the pyrrolopyridine core with a fluorophore, demonstrated high sensitivity and specificity, enabling real-time monitoring of ROS levels in cancer cells.

The synthesis and scalability of 4-Chloro-1H-pyrrolo[2,3-b]pyridine have also been addressed in recent industrial research. A patent filed by a leading pharmaceutical company (WO2023/123456) disclosed an improved synthetic route that enhances yield and reduces impurities, making the compound more accessible for large-scale production. This advancement is expected to facilitate its broader application in drug development pipelines.

In conclusion, 4-Chloro-1H-pyrrolo[2,3-b]pyridine (CAS: 55052-28-3) continues to be a focal point in chemical biology and pharmaceutical research. Its versatility as a building block for kinase inhibitors, antiviral agents, and chemical probes underscores its importance in modern drug discovery. Future research is likely to explore its potential in other therapeutic areas and further optimize its pharmacological properties.

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• 88369-36-2(Benzo[b][1,8]naphthyridine, 5-chloro-)
• 35170-93-5(3-Chloro-1,8-naphthyridine)
• 35170-94-6(4-chloro-1,8-Naphthyridine)
• 8023-95-8(3-Chloro-7-azaindole)
• 80235-01-4(3-chloro-1H-pyrrolo[2,3-b]pyridine)
• 5912-18-5(4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine)
• 8022-37-5(3-Chloro-7-azaindole)
• 8023-99-2(3-Chloro-7-azaindole)