16382-15-3

Usage

Uses

Used in Pharmaceutical Synthesis:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for the synthesis of oxazino[4,3-a]indoles via cascade addition-cyclization reactions. This application is crucial for the development of novel pharmaceutical compounds with potential therapeutic properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for the preparation of indolecarboxamides, which act as cannabinoid CB1 receptor antagonists. These antagonists have potential applications in the treatment of various disorders related to the cannabinoid system.
Used in Anti-inflammatory and Analgesic Drug Development:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is also utilized as a reactant for the preparation of indole-3-propionic acids, which possess anti-inflammatory and analgesic properties. These agents can be used in the development of drugs for the treatment of pain and inflammation.
Used in Organic Chemistry:
In organic chemistry, ETHYL 5-METHYLINDOLE-2-CARBOXYLATE serves as a reactant for Friedel-Crafts acylation with nitrobenzoyl chloride. This reaction is an important synthetic method for the formation of carbon-carbon bonds and the synthesis of various organic compounds.
Used in Oximation Reactions:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for oximation reactions, which are significant in the synthesis of complex organic molecules and the development of new chemical entities with potential applications in various industries.

InChI:InChI=1/C12H13NO2/c1-3-15-12(14)11-7-9-6-8(2)4-5-10(9)13-11/h4-7,13H,3H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 89314-29-4 2-p-tolylhydrazono-propionic acid 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 22121-86-4 ethyl 2-ethoxyacrylate 
• 29289-13-2 2-iodo-4-methylaniline 
• 66424-92-8 5-methyl-2-nitrobenzyl alcohol 
• 952016-37-4 ethyl (5-methyl-2-nitrophenyl)pyruvate 
• 89-87-2 2,4-dimethylnitrobenzene 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 106-49-0 p-toluidine 
• 95-92-1 oxalic acid diethyl ester 
• 91462-34-9 (E)-ethyl 2-(p-tolylhydrazono)propanoate 
• 10241-97-1 5-methylindole-2-carboxylic acid 
• 16382-10-8 ethyl 2-[2-(4-methylphenyl)hydrazinylidene]propanoate 

Downstream Products

• 73725-20-9 ethyl 3-(α,o-dichlorobenzyl)-5-methylindole-2-carboxylate 
• 1463-64-5 5-methyl-indole-2-carboxylic acid hydrazide 
• 1360148-58-8 [1-(4-methoxy-benzyl)-5-methyl-1H-indol-2-yl]-methanol 
• 1360148-62-4 1-(4-methoxy-benzyl)-5-methyl-1H-indole-2-carbaldehyde 
• 1360148-40-8 1-[1-(4-methoxy-benzyl)-1H-indol-2-yl]-5-methyl-hex-4-en-1-one 
• 1360148-42-0 1-[1-(4-methoxy-benzyl)-5-methyl-1H-indol-2-yl]-hex-5-en-1-ol 
• 1360148-39-5 1-[1-(4-methoxy-benzyl)-1H-indol-2-yl]-5-methyl-hex-4-en-1-ol 
• 1360148-45-3 acetic acid 1-[1-(4-methoxy-benzyl)-5-methyl-1H-indol-2-yl]-hex-5-enyl ester 
• 1360148-49-7 acetic acid 1-[1-(4-methoxy-benzyl)-1H-indol-2-yl]-5-methyl-1H-indol-2-yl-hex-5-enyl ester 
• 1360148-51-1 acetic acid 5-hydroxy-1-[1-(4-methoxy-benzyl)-5-methyl-1H-indol-2-yl]-hexyl ester 
• 1360148-54-4 1-(4-methoxy-benzyl)-5-methyl-1H-indole-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Synthesis method for preparing 2-substituted indole derivative

The invention relates to a synthesis method for preparing a 2-substituted indole derivative. The method includes the following steps: mixing aromatic amine compounds (I), ketone compounds (II) and a drying agent in an organic solvent; adding a palladium catalyst; and reacting in an aerobic weak acid environment to prepare the indole compounds (III). (I), (II) and (III) are as shown in the specification, wherein R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted phenyl, pyridyl and heterocyclic aryl; (I) can be pyridylamine, pyrimidylamine, pyridazinam or pyrazinamide which may further be substituted or unsubstituted; and the substituents are selected fromone or more C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, amino; and R2 is selected from C1-C6 alkyl, formate groups or C1-C6 alkylamide groups.

Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling

The cross-dehydrogenative coupling (CDC) reaction is an efficient strategy for indole synthesis. However, most CDC methods require special substrates, and the presence of inherent groups limits the versatility for further transformation. A carboxylic acid-promoted aerobic catalytic system is developed herein for a single-step synthesis of indoles from simple anilines and ketones. This versatile system is featured by the broad substrate scope and the use of ambient oxygen as an oxidant and is convenient and economical for both laboratory and industry applications. The existence of the labile hydrogen at C-3 and the highly transformable carbonyl at C-2 makes the indoles versatile building blocks for organic synthesis in different contexts. Computational studies based on the density functional theory (DFT) suggest that the rate-determining step is carboxylic acid-assisted condensation of the substrates, rather than the functionalization of aryl C-H. Accordingly, a pathway via imine intermediates is deemed to be the preferred mechanism. In contrast to the general deduction, the in situ formed imine, instead of its enamine isomer, is believed to be involved in the first ligand exchange and later carbopalladation of the α-Me, which shed new light on this indolization mechanism.

Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles

A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.

Three consecutive steps over the chirally modified Pt surface: Asymmetric catalytic cascade reaction of 2-nitrophenylpyruvates

The influence of the reaction conditions on the asymmetric heterogeneous cascade reaction of 2-nitrophenylpyruvates over Pt catalysts modified with cinchonidine leading to (R)-3-hydroxy-3,4-dihydroquinolin-2(1H)-one derivatives has been studied. Results of studies on the amount of acetic acid or catalyst, nature of the Pt support, kinetic examinations, effect of H2 pressure, and modifier and substrate concentrations showed that all three steps of this catalytic cascade take place on the Pt surface, with the nitro group reduction immediately following the enantioselective hydrogenation of the keto group, whereas the final intramolecular amidation was preceded by desorption after complete reduction of the substrate and re-adsorption of the corresponding intermediate.

Indoles via Knoevenagel-Hemetsberger reaction sequence

A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H-13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific - only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β- arylacrylates resulted in the formation of both the 5- and 7- substituted indoles - the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3- phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4- phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.

A tandem "on-palladium" Heck-Jeffery amination route toward the synthesis of functionalized indole-2-carboxylates

A direct synthesis of functionalized indole-2-carboxylates involving a PdII-catalyzed annulation of ortho-iodoanilines onto a vinyl ether is described. The reaction mechanism is shown to be distinct from a stepwise Heck, intramolecular amination pathway, likely involving a tandem "on-palladium" Heck-Jeffery amination process incorporating a novel intramolecular amination step.

Synthetic approaches to natural antioxidant benzastatin E, F and G analogues

For synthesis of benzastatin E, F and G analogues, the indole-2- carbaldehydes with or without substituents at C-5 position were prepared as key intermediates. Several synthetic attempts to achieve benzastatin E-G analogues were suggested using the indole-2-carbaldehyde intermediates.

Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process

A straightforward synthesis of indole-2-carboxylic esters was developed through a ligand-free copper-catalysed condensation/coupling/deformylation cascade process from 2-halo aryl aldehydes or ketones with ethyl isocyanoacetate. The reactions proceeded we

Novel triazole derivatives, process for their preparation and pharmaceutical compositions containing them

The invention relates to a compound of formula in which R1, X1, X2, X3, X4, R4, Y1, Y2 and Y3 are as defined in claim 1. These compounds are CCK-receptor agonists.