3682-74-4

Usage

Structure

An indazole derivative with a bromine atom attached to the phenyl ring

Pharmacological properties

Potential drug candidate for various therapeutic applications

Synthesis

Used as a building block in the synthesis of other organic compounds

Chemical properties and reactivity

Valuable tool in chemical and pharmaceutical research

Upstream product

• 17064-89-0 N-(4-bromophenyl)-1-(2-nitrophenyl)methanimine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 106-40-1 4-bromo-aniline 
• 589-87-7 1,4-bromoiodobenzene 
• 780-20-1 N-benzylidene-4-bromoaniline 
• 16714-25-3 2-azidobenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 3623-23-2 4-bromonitrosobenzene 
• 100-52-7 benzaldehyde 
• 144572-25-8 N-(o-bromobenzylidene)-p-bromoaniline 
• 271-44-3 benzimidazole 
• 5467-74-3 4-Bromophenylboronic acid 
• 934328-69-5 (4-bromophenyl)[(1E)-(2-nitrophenyl)methylidene]amine 

Relevant academic research and scientific papers

Cyclometalated iridium(III) complexes containing 2-phenyl-2H-indazole ligand: Synthesis, photophysical studies, and DFT calculations

Heteroleptic cyclometalated iridium(III) complexes (Ir1–Ir5) featuring piz-based ligands and acetylacetone ancillary ligand are synthesized and characterized. Their photophysical and electrochemical properties were studied, and DFT calculations were used to further support the experiment results. All the complexes emit yellow color with quantum yields of 12.2–56.5% in dichloromethane solution at room temperature, and the emission originates from a hybrid 3MLCT/3ILCT/3LLCT excited state.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

Preparation method 2 - substituted - 222H-indazole compound

The invention provides a preparation method of a 2-substituent-2H-indazole compound. With a cuprous catalyst, a coupling reaction is carried out to substituted 1H-indazole and aryliodonium salt in a low-molecular polar organic solvent to obtain a corresponding 2-substituent-2H-indazole compound, wherein the molar ratio of the 1H-indazole to the aryliodonium salt is 1:1.2. According to the method,the reaction route starts from the 1H-indazole compound which is easy to obtain; with the low-cost cuprous compound as a catalyst, the reaction condition is gentle and yield of produced target compound is high. The method also has good compatibility with various functional groups and can be widely applied to synthesize 2-substituent-2H-indazole compounds having different substituent groups. The method has important application value.

Highly efficient yellow-emitting iridium(III) complexes based on fluorinated 2-(biphenyl-4-yl)-2H-indazole ligands: Syntheses, structures, properties, and density functional theory calculations

Two new iridium (III) complexes (Ir1-Ir2) bearing different fluorinated 2-(biphenyl-4-yl)-2H-indazole-based compounds as cyclometalated ligands and Xantphos as an ancillary ligand were synthesized and fully characterized. The ultraviolet (UV)–vis absorpti

Tert-Butyl Hydroperoxide-Mediated Oxo-Sulfonylation of 2 H-Indazoles with Sulfinic Acid toward Indazol-3(2 H)-ones

A new and efficient oxo-sulfonylation protocol has been established for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a sulfonylating agent using tert-butyl hydroperoxide (TBHP) under ambient air. A series of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives were obtained in good yields. A radical reaction mechanism has been proposed for this transformation.

Regioselective C3-H Trifluoromethylation of 2 H-Indazole under Transition-Metal-Free Photoredox Catalysis

Trifluoromethyl-substituted heteroarenes are biologically active compounds and useful building blocks. In this sequence, we have developed a visible-light-promoted regioselective C3-H trifluoromethylation of 2H-indazole under metal-free conditions, which

Room-Temperature, Metal-Free, and One-Pot Preparation of 2H-Indazoles through a Mills Reaction and Cyclization Sequence

The Mills reaction and cyclization of readily available 2-aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2H-indazoles in up to 88 % yields. In the metal-free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2H-indazole could also be obtained through the one-pot sequence.

Visible-light-induced regioselective cross-dehydrogenative coupling of 2 H-indazoles with ethers

A visible-light-promoted regioselective C(sp2)-H/C(sp3)-H cross-dehydrogenative coupling between 2H-indazoles and ethers has been achieved using a catalytic amount of rose bengal as an organophotoredox-catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant at ambient temperature under aerobic conditions. A variety of C-3 oxyalkylated 2H-indazoles have been synthesized in moderate to good yields. Mechanistic studies suggest a radical pathway of the present reaction.

Direct Acyl Radical Addition to 2 H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids

A direct acyl radical addition to 2H-indazoles has been achieved for the first time, where the less-aromatic quinonoid 2H-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2H-indazoles, the current method utilizes the radical acceptability of 2H-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-acyl-2H-indazoles with three points of structural diversification in 25%-83% yields.

Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation

Malaria is a tropical parasitic disease threatening populations in tropical and sub-tropical areas. Resistance to antimalarial drugs has spread all over the world in the past 50 years, thus new drugs are urgently needed. Plasmodione (benzylmenadione series) has been identified as a potent antimalarial early lead drug, acting through a redox bioactivation on asexual and young sexual blood stages. To investigate its metabolism, a series of plasmodione-based tools, including a fully 13C-labelled lead drug and putative metabolites, have been designed and synthesized for drug metabolism investigation. Furthermore, with the help of UHPLC-MS/MS, two of the drug metabolites have been identified from urine of drug-treated mice.