Production Method 1

2378746-97-3

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  2 h, 65 °C

Reference

Preparation of dihydroisoquinoline-2(1H)-carboxamides and related compounds and their use in treating medical conditions

, World Intellectual Property Organization, , ,

Production Method 2

535-80-8

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetramethylammonium bromide ,  Methanesulfonic anhydride Solvents: 1,2-Dimethoxyethane ;  rt; 18 h, rt

Reference

Indole compound, preparation and pharmaceutical composition and application thereof

, China, , ,

Production Method 3

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Methanesulfonic anhydride Solvents: Dimethylformamide ;  rt → 0 °C; 0 °C; 0 °C → rt; 6 h, rt
1.2 Reagents: Water
1.3 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Preparation of 3-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl phenyl ureas for treating conditions mediated by at least one BRaf family kinase

, World Intellectual Property Organization, , ,

Production Method 4

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Trimethylammonium bromide ,  Methanesulfonic anhydride Solvents: Chloroform ;  0 °C → 25 °C; 16 h, 25 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  0.5 h, neutralized, cooled

Reference

Preparation of aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 5

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Methanesulfonic anhydride Solvents: 1,2-Dimethoxyethane ;  5 min, 0 °C; 0 °C → rt; 18 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, cooled

Reference

Discovery of GSK1070916, a Potent and Selective Inhibitor of Aurora B/C Kinase

Adams, Nicholas D.; Adams, Jerry L.; Burgess, Joelle L.; Chaudhari, Amita M.; Copeland, Robert A.; et al, Journal of Medicinal Chemistry, 2010, 53(10), 3973-4001

Production Method 6

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Methanesulfonic anhydride Solvents: Dimethylformamide ;  6 h, rt

Reference

Knowledge-based design of 7-azaindoles as selective B-Raf inhibitors

Tang, Jun; Hamajima, Toshihiro; Nakano, Masato; Sato, Hideyuki; Dickerson, Scott H.; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(16), 4610-4614

Production Method 7

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Methanesulfonic anhydride Solvents: Dimethylformamide ;  rt → 0 °C; 0 °C; 0 °C → rt; 6 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Preparation of novel pyrrolo[2,3-b]pyridine derivatives as histamine c-Met kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 8

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Methanesulfonic anhydride Solvents: Dimethylformamide ;  rt → 0 °C; 0 °C; 0 °C → rt; 6 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Preparation of pyrrolo[2,3-b]pyridines as inhibitors of Akt activity

, World Intellectual Property Organization, , ,

Production Method 9

535-80-8

287384-82-1

942920-55-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Water ;  rt; pH 10, rt
1.2 Reagents: Tetramethylammonium bromide ,  Methanesulfonic anhydride Solvents: Dimethylformamide ,  Acetonitrile ;  cooled; rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  7 °C

Reference

Synthesis and activity evaluation of PARP-1 inhibitors with azaindole skeleton

Zhou, Jie; Zhu, Zhi-xiang; Chen, Xiao-guang; Xu, Bai-ling, Yaoxue Xuebao, 2013, 48(12), 1792-1799

Production Method 10

942920-55-0

Reaction Conditions

Reference

Pyrrolopyridine carboxylic acid derivatives

, United States, , ,

Production Method 11

942920-55-0

Reaction Conditions

Reference

Preparation of pyrrolopyridine carboxylic acid derivatives for the treatment of neurological and psychiatric disorder

, World Intellectual Property Organization, , ,

Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate Raw materials

• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 4-bromo-1-(phenylsulfonyl)-, ethyl ester
• 3-Chlorobenzoic acid
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester, 7-oxide

Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate Preparation Products

• Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (942920-55-0)

• 1. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 2. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 3. Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid
  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 4. Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon?
  Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng Pu Chem. Commun., 2019,55, 3963-3966
• 5. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696

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

Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate: A Comprehensive Overview

Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, with the CAS number 942920-55-0, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound belongs to the class of pyrrolopyridines, which are known for their unique structural properties and potential applications in drug discovery. The molecule features a bromine substituent at the 4-position of the pyrrolopyridine ring system, along with an ethyl ester group attached to the carboxylic acid moiety at the 2-position. These structural elements contribute to its distinct chemical reactivity and biological activity.

Recent studies have highlighted the importance of pyrrolopyridines in medicinal chemistry, particularly as scaffolds for designing bioactive molecules. Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate has been explored as a potential lead compound in the development of new therapeutic agents. Its brominated structure makes it a promising candidate for further functionalization, enabling researchers to investigate its role in various biological pathways.

The synthesis of Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate involves a multi-step process that typically includes cyclization reactions and subsequent bromination. The exact synthetic route may vary depending on the starting materials and desired stereochemistry. Researchers have optimized these methods to achieve high yields and purity, ensuring that the compound is suitable for downstream applications such as bioassays and pharmacokinetic studies.

In terms of biological activity, Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate has shown promise in several assays targeting key enzymes and receptors. For instance, recent findings suggest that it exhibits moderate inhibitory activity against certain kinases, which are critical in cell signaling pathways. This makes it a valuable tool for studying disease mechanisms and developing targeted therapies.

Moreover, the compound's structural versatility allows for further modifications to enhance its pharmacokinetic properties. For example, researchers have explored the replacement of the ethyl ester group with other functional groups to improve solubility and bioavailability. These modifications are essential for translating laboratory findings into clinically relevant compounds.

From an analytical standpoint, Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate can be characterized using a variety of techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography. These methods provide insights into its molecular structure, purity, and stability under different conditions.

Looking ahead, the continued exploration of Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate is expected to yield further discoveries in its application as a drug candidate. Its unique combination of structural features and biological activity positions it as a valuable asset in the ongoing quest for innovative therapeutic solutions.

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