112398-75-1

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-1-METHYLINDOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its unique structural properties. Its ability to be modified and incorporated into complex molecules makes it valuable in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 5-CHLORO-1-METHYLINDOLE is utilized as a versatile building block for the synthesis of a wide range of organic compounds. Its reactivity and functional groups allow for various chemical reactions, leading to the creation of novel molecules with potential applications in different industries.
Used in Research and Development:
5-CHLORO-1-METHYLINDOLE is employed as a research compound in academic and industrial laboratories. Its unique properties and potential for modification make it an attractive candidate for studying chemical reactions, exploring new synthetic routes, and developing innovative applications.
Used in Chemical Production:
As a crucial intermediate, 5-CHLORO-1-METHYLINDOLE is used in the large-scale production of various chemical products. Its versatility and compatibility with different chemical processes contribute to the efficiency and effectiveness of manufacturing operations.
Used in Agrochemical Industry:
5-CHLORO-1-METHYLINDOLE may also find applications in the agrochemical industry, where it can be used as a starting material for the synthesis of pesticides, herbicides, or other agricultural chemicals. Its unique structure and reactivity can contribute to the development of more effective and environmentally friendly products.

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 74-88-4 methyl iodide 
• 32617-55-3 5-chloro-1-p-toluenesulfonylindole 
• 865-33-8 potassium methanolate 
• 10075-50-0 5-bromo-1H-indole 
• 25658-80-4 5-chloro-2,3-dihydroindole 
• 26663-50-3 5-chloro-1-methylindoline 
• 616-38-6 carbonic acid dimethyl ester 
• 1352622-03-7 1-bromo-2-[(4-chlorophenyl)methylamino]ethanesulfonic acid 2,4,6-trichlorophenyl ester 
• 1352621-91-0 1-bromo-2-(4-chlorophenylamino)ethanesulfonic acid 2,4,6-trichlorophenyl ester 
• 210536-10-0 N-(4-Chloro-2-vinyl-phenyl)-2,2,2-trifluoro-N-methyl-acetamide 
• 932-96-7 N-methyl(p-chloroaniline) 
• 210536-18-8 (4-Chloro-2-vinyl-phenyl)-methyl-amine 
• 181651-29-6 N-(4-chlorophenyl)-N-methylethenesulfinamide 

Downstream Products

• 1018914-02-7 5-chloro-1-methyl-2-phenyl-1H-indole 
• 1273594-89-0 5-chloro-3-dimethylphenylsilyl-1-methylindole 
• 441715-86-2 C₃₁H₃₃ClFN₃O₅ 
• 441712-68-1 trans-4-[1-[[2-(5-chloro-1-methyl-3-indolyl)-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 1440662-94-1 (E)-3-(5-chloro-1-methyl-1H-indol-3-yl)-1-phenylprop-2-en-1-one 
• 1579298-93-3 N-(5-chloro-1-methyl-3-(4-nitrophenylimino)indolin-2-ylidene)-4-nitrobenzenamine 
• 1607841-66-6 1-methyl-5-(4-methylphenyl)indole 
• 60434-13-1 5-chloro-1-methylindoline-2, 3-dione 

Relevant academic research and scientific papers

Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system

A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4? molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.

Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position

Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).

Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property

A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.

ARYL HYDROCARBON RECEPTOR ACTIVATORS

Small molecule AhR ligands are disclosed. The ligands can induce the differentiation of Tr1 cells to suppress pathogenic immune responses without inducing nonspecific immune suppression. Methods of treatment of autoimmune diseases using the AhR ligands are also disclosed.

Tandem iridium-catalyzed decarbonylative c-h activation of indole: Sacrificial electron-rich ketone-assisted bis-arylsulfenylation

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp?IrCl2]2) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.

Assembly of polycyclic N-heterocycles: Via copper-catalyzed cycloamination of indolylquinones and aromatic amines

The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.

Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles

A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

Visible-Light-Induced, Base-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides

We report a simple and efficient visible-light-induced transition-metal-free hydrogenation of aryl halides. The combined visible light and base system is used to initiate the desired radical-mediated hydrogenation. A variety of aryl fluorides, chlorides, bromides, and iodides could be reduced to the corresponding (hetero)arenes with excellent yields under mild conditions. Various functional groups and other heterocyclic compounds are tolerated.