66866-01-1

Usage

Chemical class

Indole derivatives

Explanation

1H-Indole, 7-chloro-2-phenylis a compound that belongs to the class of indole derivatives, which are heterocyclic organic compounds.

Explanation

It consists of a carbon-nitrogen ring structure, which is characteristic of heterocyclic organic compounds.

Explanation

The indole ring has a chloro (-Cl) group at position 7 and a phenyl (-C6H5) group at position 2.

Explanation

1H-Indole, 7-chloro-2-phenylhas been studied for its potential pharmacological properties, including its ability to inhibit the growth of microorganisms and its potential to combat cancer cells.

Explanation

1H-Indole, 7-chloro-2-phenyl- serves as a starting material or building block in the synthesis of various other biologically active compounds and pharmaceuticals, making it valuable in the field of medicinal chemistry.

Explanation

1H-Indole, 7-chloro-2-phenylhas been found to exhibit unique and interesting properties in chemical and material science research, making it a versatile molecule in these fields of study.

Structure

Heterocyclic organic compound

Substituents

Chloro and phenyl groups

Pharmacological properties

Antimicrobial and anticancer activities

Synthesis building block

Used in the synthesis of biologically active compounds and pharmaceuticals

Chemical and material science research

Exhibits interesting properties

Upstream product

• 64605-35-2 1-(2-amino-3-chlorophenyl)-2-chloroethan-1-one 
• 100-59-4 phenylmagnesium chloride 
• 536-74-3 phenylacetylene 
• 615-41-8 2-iodochlorobenzene 
• 19433-17-1 (E)‐1‐phenylethan‐1‐one O‐acetyl oxime 
• 613-91-2 acetophenone oxime 
• 19433-17-1 acetophenone O-acetyloxime 
• 100-47-0 benzonitrile 
• 85089-31-2 3-chloro-2-fluorotoluene 
• 95-51-2 o-chloroaniline 
• 53924-05-3 7-chloro-1H-indole 
• 613-94-5 benzoic acid hydrazide 
• 98-09-9 benzenesulfonyl chloride 
• 72373-82-1 1-chloro-2-fluoro-3-iodobenzene 

Downstream Products

• 1060749-18-9 (7-chloro-2-phenylindol-3-yl)glyoxylyl chloride 
• 1025807-12-8 4-(7-chloro-2-phenyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 94303-62-5 7-chloro-3-morpholin-4-ylmethyl-2-phenyl-indole 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Method for synthesizing 2-substituted indole compound from iodobenzene and oxime ester under catalysis of palladium

The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a 2-substituted indole compound from iodobenzene and oxime ester under the catalysis of palladium. The method comprises the following steps of reacting an oxime ester compound with iodobenzene under the action of a palladium catalyst, a phosphine ligand and norbornene by taking an organic solvent as a reaction medium in a protective atmosphere, and carrying out subsequent treatment to obtain the 2-substituted indole compound. According to the method, palladium is used as a catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the oxime ester compound is used as a raw material, and the method has the advantages of cheap and easily-prepared raw materials, simple operation, mild reaction conditions and the like.

Synthetic method of 2-substituted indoles compounds

The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.

Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles

Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition-metal-free assembly of 2-aryl indoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.

Indole-3-carbonitriles as DYRK1A inhibitors by fragment-based drug design

Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer's disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3, 2-c]quinoline-6-carboxy

Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles

An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.

Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides

A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.

Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO

The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is

Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant

A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.

The sequential reactions of tetrazoles with bromoalkynes for the synthesis of (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides and 2-arylindoles

2-Arylindoles were prepared by a sequential reaction of Ag-catalyzed α-addition-Pd-catalyzed C-H bond functionalization of tetrazoles with bromoalkynes. A stereocontrolled Ag-catalyzed α-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate (Z)-N-(2-bromo-1- vinyl)-N-arylcyanamides, which were subsequently converted into 2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C-H bond functionalizations.