6260-97-5

Usage

Uses

Used in Recreational Drug Industry:
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone is used as a psychoactive substance for recreational purposes due to its ability to mimic the effects of natural cannabis. Its potent agonist activity on the CB1 receptor results in hallucinogenic effects similar to those of THC, making it a popular choice among individuals seeking altered states of consciousness.
However, it is important to note that the use of (4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone for recreational purposes is illegal in many countries due to its classification as a controlled substance. The potential for abuse and associated health risks have led to increased scrutiny and regulation by law enforcement and regulatory authorities.

Upstream product

• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 122-01-0 4-chloro-benzoyl chloride 
• 128368-43-4 2-isopropenyl-4-methoxyaniline 
• 68267-68-5 2-allyl-4-methoxyaniline 
• 74-11-3 para-chlorobenzoic acid 
• 104-94-9 4-methoxy-aniline 
• 71954-46-6 N-allyl-4-methoxyaniline 

Downstream Products

• 1601-18-9 indomethacin methyl ester 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 76812-74-3 Benzyl--<1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3>>glykolat 
• 70422-77-4 Chloro-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid benzyl ester 
• 70180-40-4 Benzyl<1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3>glykolat 

Relevant academic research and scientific papers

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.

Application of hypervalent iodine reagent-mediated in preparation of indole derivatives

The invention relates to application of hypervalent iodine reagent-mediated in preparation of indole derivatives, in particular to the application of organic trivalent iodine reagent iodoyl benzene aminosulfonate in preparing N-protected 2-substituted indole compounds and indomethacin, zidometacin, pravadoline. The invention relates to the application of organic trivalent iodine reagent iodoyl benzene aminosulfonate in preparing N-protected 2-substituted indole compounds, and the reaction undergoes functional group exchange of a substrate. In addition, iodoyl benzene aminosulfonate plays two important roles in this application, as an oxidant and as Bronsted acid. The application has the advantages of good regioselectivity, wide substrate range, mild conditions, simple operation and amplification of experimental steps. The application of the organic trivalent iodine reagent iodoyl benzene aminosulfonate in the preparation of indomethacin, zidomeprin and pravadoline provided by the invention has the advantages of high synthesis efficiency, simple operation and the like.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.

Straightforward protocol for the efficient synthesis of varied N 1-acylated (aza)indole 2-/3-alkanoic acids and esters: Optimization and scale-up

A library of approximately 40 N1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2′-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets.