39203-20-8

Usage

Uses

N-(Methoxycarbonyl)indole, Indole-1-carboxylic acid methyl ester is used as a reactant in various chemical synthesis processes for the development of different compounds and materials.
Used in Pharmaceutical Industry:
N-(Methoxycarbonyl)indole, Indole-1-carboxylic acid methyl ester is used as a reactant for the preparation of Bcl Inhibitor Obatoclax. This application is significant because Obatoclax is a potent inhibitor of the anti-apoptotic Bcl-2 protein family, which plays a crucial role in the development and progression of various cancers.
Used in Organic Synthesis:
N-(Methoxycarbonyl)indole, Indole-1-carboxylic acid methyl ester is used as a reactant for the preparation of tetracyclic indolines. These complex indole-based structures are valuable in the synthesis of various bioactive compounds, including pharmaceuticals and agrochemicals.
Used in Friedel-Crafts Alkylation:
N-(Methoxycarbonyl)indole, Indole-1-carboxylic acid methyl ester is used as a reactant for Friedel-Crafts alkylation reactions of indoles. This versatile reaction allows for the introduction of alkyl groups to the indole nucleus, leading to the formation of a wide range of indole-based compounds with diverse applications in the chemical and pharmaceutical industries.
Used in Oxidative Free Radical Reactions:
N-(Methoxycarbonyl)indole, Indole-1-carboxylic acid methyl ester is used as a reactant for oxidative free radical reactions. These reactions are essential in the synthesis of various indole-based compounds with modified properties, which can be utilized in different applications, such as the development of new materials, pharmaceuticals, and agrochemicals.

Upstream product

• 23206-21-5 methyl 2-vinylaniline-N-carboxylate 
• 546-67-8 lead(IV) tetraacetate 
• 615-43-0 2-iodophenylamine 
• 120-72-9 indole 
• 616-38-6 carbonic acid dimethyl ester 
• 79-22-1 methyl chloroformate 
• 911022-64-5 N-(methoxycarbonyl)-2-vinylformanilide 

Downstream Products

• 148323-46-0 2-aza-3,4-benzo-N-carbmethoxy-bicyclo-<3.1.0>hex-3-ene 
• 91476-99-2 3-(2,4,6-Trimethyl-phenyl)-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid methyl ester 
• 91477-00-8 3-(2,4,6-Trimethyl-phenyl)-3a,8b-dihydro-isoxazolo[4,5-b]indole-4-carboxylic acid methyl ester 
• 942-24-5 3-methoxycarbonylindole 
• 58881-41-7 6H,13H-pyrazino<1,2-a:4,5-a'>diindole-6,13-dione 
• 20921-96-4 methyl 2-(2-cyanophenyl)acetate 
• 120-72-9 indole 
• 1001162-89-5 1-(N-methoxycarbonyl)indole-2-boronic acid 
• 67-56-1 methanol 
• 803712-70-1 tert-butyl 2-(5-formyl-4-methoxy-1H-pyrrol-2-yl)-1H-indole-1-carboxylate 
• 91477-22-4 N-methoxycarbonyl-N'(2,4,6-trimethylphenyl)indole-3-carboxamide 
• 82430-59-9 3-(2,4,6-Trimethyl-phenyl)-4,8b-dihydro-3aH-isoxazolo[4,5-b]indole 
• 82414-32-2 N(2,4,6-trimethylphenyl)indole-3-carboxamide 
• 67060-92-8 (1H-indole-1,3-diyl)bis(phenylmethanone) 

Relevant academic research and scientific papers

Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bon

Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions

The ionic liquid, tributylmethylammonium methylcarbonate, has been employed as a catalytic base for clean N-methylation of indole with dimethylcarbonate. The reaction conditions were optimised under microwave heating to give 100% conversion and 100% selectivity to N-methylindole, and subsequently transferred to a high temperature/high pressure (285 °C/150 bar) continuous flow process using a short (3 min) residence time and 2 mol% of the catalyst to efficiently methylate a variety of different amines, phenols, thiophenols and carboxylic acid substrates. The extremely short residence times, versatility, and high selectivity have significant implications for the synthesis of a wide range of pharmaceutical intermediates, as high product throughputs can be obtained via this scalable continuous flow protocol. It has also been shown that the ionic liquid can be generated in situ from tributylamine, which has the net effect of transforming an ineffective stoichiometric base into a highly efficient catalyst for this broad class of reactions.

Synthesis of indolylindolines mediated by t-BuNH2

An improved synthesis of N1-carbomethoxylated indolylindolines 2 from 5-substituted indoles 1, by replacing the previously employed strong acids or toxic metals with t-BuNH2/MeOCOCl in CH2Cl2/H2O, is described.

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.