Production Method 1

1192217-76-7

941714-57-4

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  cooled; 5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  cooled
1.3 Reagents: Ammonia Solvents: Methanol ,  Water ;  1 h, rt

Reference

Pyrrolotriazine derivatives as PI3K inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 2

1192217-76-7

941714-57-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  5 h, 65 °C

Reference

Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji-Trost Process

Steeds, Hannah G.; Knowles, Jonathan P.; Yu, Wai L.; Richardson, Jeffery; Cooper, Katie G.; et al, Chemistry - A European Journal, 2020, 26(63), 14330-14334

Production Method 3

1192217-76-7

941714-57-4

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  4 h, rt

Reference

Preparation of pyrrolotriazinone derivatives as therapeutic PI3K inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

1097834-88-2

941714-57-4

Reaction Conditions

1.1 Reagents: Zinc bromide Solvents: Dichloromethane ;  rt → reflux; 2 h, reflux; cooled
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Process for preparation of compound for treating hepatitis B

, China, , ,

Production Method 5

1097834-88-2

941714-57-4

Reaction Conditions

1.1 Reagents: Zinc bromide

Reference

A Total Synthesis of the Marine Alkaloid Ningalin B from (S)-Proline

Hasse, Katrin; Willis, Anthony C.; Banwell, Martin G., Australian Journal of Chemistry, 2009, 62(7), 683-691

Production Method 6

1097834-88-2

941714-57-4

Reaction Conditions

1.1 Reagents: Zinc bromide Solvents: Dichloromethane ;  5 h, 18 °C

Reference

Attempts to Mimic Key Bond-Forming Events Associated with the Proposed Biogenesis of the Pentacyclic Lamellarins

Axford, Lorraine C.; Holden, Kate E.; Hasse, Katrin; Banwell, Martin G.; Steglich, Wolfgang; et al, Australian Journal of Chemistry, 2008, 61(2), 80-93

Production Method 7

1192217-76-7

941714-57-4

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  0 °C; 4 h, rt

Reference

Pyrrolotriazinone derivatives as PI3K inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 8

1192217-76-7

941714-57-4

Reaction Conditions

1.1 Reagents: Propargyl alcohol Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Triethylamine ;  20 h, 80 °C

Reference

Synthesis of 4,5-disubstituted pyrano[3,4-b]pyrrol-7(1H)-ones via Sonogashira-Hagihara cross-coupling of N-benzenesulfonyl-3-bromo-1H-pyrrole-2-carboxylate and subsequent iodine-mediated cyclization

Fukuda, Tsutomu; Komure, Minoru; Onodera, Gen; Kimura, Masanari; Iwao, Masatomo, Heterocycles, 2018, 97(2), 916-930

Production Method 9

145821-55-2

941714-57-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  cooled; overnight, rt

Reference

Preparation of amide compounds containing adamantane moiety as 11β-HSD1 inhibitors

, World Intellectual Property Organization, , ,

Methyl 3-bromo-1H-pyrrole-2-carboxylate Raw materials

• Methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate
• 1-tert-butyl 2-methyl 3-bromo-1H-pyrrole-1,2-dicarboxylate
• 3-bromo-1H-Pyrrole-2-carboxylic acid

Methyl 3-bromo-1H-pyrrole-2-carboxylate Preparation Products

• Methyl 3-bromo-1H-pyrrole-2-carboxylate (941714-57-4)

• 1. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 2. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 3. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 4. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 5. 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

Methyl 3-bromo-1H-pyrrole-2-carboxylate: A Comprehensive Overview

Methyl 3-bromo-1H-pyrrole-2-carboxylate, also known by its CAS number 941714-57-4, is a compound of significant interest in the field of organic chemistry. This compound is a derivative of pyrrole, a five-membered aromatic heterocycle, and it features a bromine atom at the 3-position and a methyl ester group at the 2-position. The structure of this compound is represented by the formula C6H5BrO2, and it is widely studied for its potential applications in various chemical reactions and synthesis pathways.

The synthesis of Methyl 3-bromo-1H-pyrrole-2-carboxylate typically involves the bromination of pyrrole derivatives. Recent studies have shown that this process can be optimized using catalytic systems or microwave-assisted techniques, which not only improve reaction efficiency but also reduce environmental impact. For instance, researchers have demonstrated that the use of palladium catalysts can significantly enhance the regioselectivity of bromination reactions, leading to higher yields of the desired product.

In terms of applications, Methyl 3-bromo-1H-pyrrole-2-carboxylate has been utilized as an intermediate in the synthesis of various bioactive compounds. Its bromine atom serves as an excellent leaving group, making it ideal for substitution reactions. Recent advancements in medicinal chemistry have highlighted its role in the development of potential anticancer agents. For example, studies published in the Journal of Medicinal Chemistry have shown that derivatives of this compound exhibit promising cytotoxic activity against several cancer cell lines.

Moreover, Methyl 3-bromo-1H-pyrrole-2-carboxylate has found applications in materials science, particularly in the synthesis of conducting polymers. The aromaticity and electron-withdrawing groups present in this compound make it a suitable candidate for polymerization reactions. Recent research has explored its use in creating novel materials for electronic devices, such as organic light-emitting diodes (OLEDs) and flexible electronics.

The stability and reactivity of Methyl 3-bromo-1H-pyrrole-2-carboxylate have been extensively studied under various conditions. It is known to be stable under normal storage conditions but can undergo decomposition under harsh acidic or basic environments. Recent investigations have also revealed its susceptibility to photodegradation, which has implications for its storage and handling in industrial settings.

In terms of toxicity and environmental impact, studies on CAS No. 941714-57-4 suggest that it exhibits moderate toxicity to aquatic organisms. However, further research is required to fully understand its environmental fate and potential risks to ecosystems.

Looking ahead, the demand for Methyl 3-bromo-1H-pyrrole-2-carboxylate is expected to grow with advancements in pharmaceutical research and materials science. Its unique chemical properties make it a valuable building block for synthesizing complex molecules with diverse functionalities.

• 53636-56-9(methyl 3-bromopyridine-2-carboxylate)
• 433267-55-1(Ethyl 4-bromo-1H-pyrrole-2-carboxylate)
• 434319-41-2(Ethyl 3-bromopicolinate)
• 61830-10-2(2,6-Pyridinedicarboxylic acid, 3,5-dibromo-, dimethyl ester)
• 220664-31-3(Methyl 3-bromo-1H-indole-2-carboxylate)
• 316808-11-4(Dimethyl 3-bromopyridine-2,6-dicarboxylate)
• 1215860-20-0(methyl 5-bromo-6-methylpyridine-2-carboxylate)
• 145821-55-2(3-bromo-1H-Pyrrole-2-carboxylic acid)
• 934-05-4(Methyl 4-bromo-1H-pyrrole-2-carboxylate)
• 61830-41-9(2-Pyridinecarboxylic acid, 3,5-dibromo-, methyl ester)