23746-79-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-CHLOROPHENYL)-1H-INDOLE is used as a building block for the synthesis of various pharmaceuticals and biologically active molecules due to its unique structural features and potential pharmacological activities.
Used in Antifungal Applications:
2-(2-CHLOROPHENYL)-1H-INDOLE is used as a potential antifungal agent, with its pharmacological activities being studied for effectiveness against fungal infections.
Used in Research and Development:
2-(2-CHLOROPHENYL)-1H-INDOLE is used as a target of interest for further research and development in various fields, including pharmaceuticals, due to its potential applications and properties.

Upstream product

• 120-72-9 indole 
• 694-80-4 2-bromo-1-chlorobenzene 
• 615-41-8 2-iodochlorobenzene 
• 45750-59-2 2-chlorobenzenesulphinic acid 
• 873-31-4 2-chlorophenylacetylene 
• 615-43-0 2-iodophenylamine 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 52670-38-9 2-ethynylaniline 
• 1201632-24-7 2-((2-chlorophenyl)ethynyl)aniline 
• 80805-53-4 2-chlorophenyl α-(2-nitrobenzyl) ketone 
• 88-72-2 1-methyl-2-nitrobenzene 
• 89-98-5 2-chloro-benzaldehyde 
• 66107-10-6 2-chloro-2'-nitro-stilbene 
• 3900-89-8 2-Chlorobenzeneboronic acid 

Downstream Products

• 107917-54-4 2-(2-chlorophenyl)-1-methyl-1H-indole 
• 1224199-97-6 5,6-diphenylindolo[2,1-a]isoquinoline 
• 109811-32-7 [2-(2-chloro-phenyl)-1-methyl-indol-3-yl]-glyoxylic acid dimethylamide 
• 109934-06-7 1-[2-(2-chloro-phenyl)-1-methyl-indol-3-yl]-2-dimethylamino-ethanol 

Relevant academic research and scientific papers

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.

A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder

An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.

Metal-Free Double Csp2-H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes

A metal-free strategy for the synthesis of benzocarbazoles from 2-arylindoles and aryl ketones is developed. Various 2-aryl-3-vinyl-indoles were generated in situ through dehydrative condensation of aryl ketones and indoles. These key intermediates could be selectively converted into the corresponding benzo[a]carbazoles via a direct cyclization process between two Csp2-H bonds. Furthermore, terminal alkynes also could be used as the versatile C2 source to afford the corresponding products in good yields.

Pd-catalyzed C–H bond activation of Indoles for Suzuki reaction

Abstract: We present a practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C–H bond activation by electrophilic Pd(TFA) 2 catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields. The protocol works for benzofuran, pyrrole and thiophene also. Graphic abstract: Selective C-2 arylation of heterocycles using Pd(II) catalyst via C–H activation was performed under ambient condition. C3–C2 migration of organopalladium intermediate controls the reaction pathway.[Figure not available: see fulltext.].

Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates

A series of alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of substituted nitro compounds to afford heterocycles, especially indoles. Phenyl formate was found to be the most effective, and it allowed the desired products to be obtained in excellent yields, often higher than those previously reported with pressurized CO. Through detailed experiments and kinetic studies, we were able to discern between metal-catalyzed and base-mediated activation of phenyl formate and confirmed that just the base was effective in catalyzing its decarbonylation.

Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1

In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.

On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.

The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons

A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.