3377-71-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 3177, 1983 DOI: 10.1021/ja00348a036Organic Syntheses, Coll. Vol. 6, p. 104, 1988

InChI:InChI=1/C15H13N/c1-2-6-13(7-3-1)12-16-11-10-14-8-4-5-9-15(14)16/h1-11H,12H2

Upstream product

• 120-72-9 indole 
• 100-44-7 benzyl chloride 
• 121195-60-6 1-benzyl-indole-2,3-dicarboxylic acid 
• 7579-36-4 dibenzyl oxalate 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 6037-73-6 1-benzyl-2,3-dihydro-1H-indole 
• 104501-75-9 N-benzylindoline-2-thione 
• 124337-33-3 1-(1H-benzotriazol-1-yl-methyl)-1H-indole 
• 87587-25-5 N-benzyl-2-[2-(trimethylsilyl)acetylenyl]aniline 
• 28284-05-1 N-benzoylisatin 
• 758640-21-0 N-Benzylaniline 
• 107-21-1 ethylene glycol 
• 102-71-6 triethanolamine 

Downstream Products

• 16571-59-8 1-benzyl-3-(2-pyridin-4-yl-ethyl)-indole 
• 125031-77-8 2,5-bis(1-benzyl-2-indolyl)-3,6-dimethylpyrazine 
• 3377-72-8 2-benzylindole 
• 200564-57-4 5-Benzyl-5H-pyridazino[4,5-b]indole-1,4-dicarboxylic acid dimethyl ester 
• 405873-13-4 (R)-3-(1-benzyl-1H-indol-3-yl)-butanal 
• 461677-86-1 1,1'-dibenzyl-1,3-dihydro-1'H-[3,3']biindolyl-2-one 
• 524035-97-0 (1-benzylindol-3-ylsulfanyl)acetic acid 
• 52604-15-6 1-benzyl-2-phenyl-1H-indole 
• 1217-89-6 1-benzylisatin 

Relevant academic research and scientific papers

An efficient method for the N-debenzylation of aromatic heterocycles

The N-debenzylation of aromatic heterocycles such as substituted pyrroles and indoles, having functional groups like ester, amide, halo, and nitrile, by using sodium in liquid ammonia in the presence of t-BuOH at -78°C cleanly affords N-debenzylated aromatic heterocycles in good yields.

Gold(I)-Catalysed Hydroarylation of 1,3-Disubstituted Allenes with Efficient Axial-to-Point Chirality Transfer

Hydroarylation of enantioenriched 1,3-disubstituted allenes has the potential to proceed with axial-to-point chirality transfer to yield enantioenriched allylated (hetero)aryl compounds. However, the gold-catalysed intermolecular reaction was previously reported to occur with no chirality transfer owing to competing allene racemisation. Herein, we describe the development of the first intermolecular hydroarylations of allenes to proceed with efficient chirality transfer and summarise some of the key criteria for achieving high regio- and stereoselectivity.

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.

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.

A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones

A general strategy for the synthesis of indolyl cyclobutanones via a tandem Bronsted acid catalyzed 2-hydroxycyclobutanone activation-indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a–c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa–ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.

N-2-pyrimidyl-3-fluoroindole compound and preparation method and application thereof

The preparation method of the N-2-pyrimidinyl-3-fluoroindole compound shown in the formula (I) comprises the following steps: by taking an acetonitrile solvent as a reaction medium, adding the N-2-pyrimidinyl indole compound shown in the formula (III), se

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

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%).

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

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