227960-12-5

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate for the synthesis of various pharmaceuticals and organic compounds. Its unique chemical structure allows it to be a versatile building block in the development of new drugs and bioactive molecules, contributing to the advancement of medicinal chemistry.
Used in Chemical Industry:
5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a valuable chemical compound in the chemical industry. Its potential applications include the production of functional materials and the development of new chemical processes, showcasing its importance in the synthesis and modification of various organic compounds.
Used in Research and Development:
5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER is utilized as a fundamental component in research and development processes. Its unique properties make it an essential tool for scientists and researchers working on the creation of innovative drugs and functional materials, driving the progress of scientific discovery and technological innovation in the pharmaceutical and chemical sectors.

InChI:InChI=1/C11H11NO2/c1-7-3-4-10-8(5-7)9(6-12-10)11(13)14-2/h3-6,12H,1-2H3

Upstream product

• 227959-99-1 methyl 1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxylate 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 10242-02-1 5-methyl-1H-indole-3-carboxylic acid 
• 1377936-23-6 3-(4-{[1-(3,4-Dimethyl-benzyl)-5-methyl-1H-indole-3-carbonyl]-amino}-benzylamino)-propionic acid 
• 1377936-42-9 1-(3,4-dimethylbenzyl)-N-(4-formylphenyl)-5-methyl-1H-indole-3-carboxamide 
• 1377936-39-4 1-(3,4-dimethylbenzyl)-N[4-(hydroxymethyl)phenyl]-5-methyl-1H-indole-3-carboxamide 
• 1377936-32-7 4-(5-(1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde 
• 1377936-30-5 (4-(5-(1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol 
• 1377936-27-0 1-(3,4-dimethylbenzyl)-5-methyl-1H-indole-3-carboxylic acid 
• 1377935-90-4 1-(4-{5-[1-(3,4-dimethylbenzyl)-5-methyl-1H-indol-3-yl]-1,2,4-oxadiazol-3-yl}benzyl)azetidine-3-carboxylic acid 
• 1377936-25-8 methyl 1-(3,4-dimethylbenzyl)-5-methyl-1H-indole-3-carboxylate 

Relevant academic research and scientific papers

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

A New Method for the Synthesis of 3-Substituted Indoles

Starting from readily accessible nitrones and electron-deficient acetylenes, a highly efficient and versatile synthetic protocol for 3-substituted indoles has been developed.

Aryliminopropadienone-C-Amidoketenimine-Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction

Imidoylketenes 11 and oxoketenimines 12 are generated by flash vacuum thermolysis of Meldrum's acid derivatives 9, pyrrolediones 17 and 18, and triazole 19 and are observed by IR spectroscopy. Ketenimine-3-carboxylic acid esters 12a are isolable at room temperature. Ketenes 11 and ketenimines 12 undergo rapid interconversion in the gas phase, and the ketenes cyclize to 4-quinolones 13. When using an amine leaving group in Meldrum's acid derivatives 9c, the major reaction products are aryliminopropadienones, ArN=C=C=C=O (15). The latter react with 1 equiv of nucleophile to produce ketenimines 12 and with 2 equiv to afford malonic acid imide derivatives 16. N-Arylketenimine-C-carboxamides 12c cyclize to quinolones 13c via the transient amidinoketenes 11c at temperatures of 25-40 °C. This implies rapid interconversion of ketenes and ketenimines by a 1,3-shift of the dimethylamino group, even at room temperature. This interconversion explains previously poorly understood outcomes of the ynamine-isocyanate reaction. The solvent dependence of the tautomerism of 4-quinolones/4-quinolinols is discussed. Rotational barriers of NMe2 groups in amidoketenimines 12c and malonioc amides and amidines 16 (24) are reported.