143952-53-8

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 616-38-6 carbonic acid dimethyl ester 
• 79-22-1 methyl chloroformate 
• 52562-18-2 2-(prop-1-en-1-yl)aniline 
• 1501966-66-0 methyl N-[2-(3-iodoprop-1-yn-1-yl)phenyl]carbamate 
• 1184039-97-1 methyl N-[2-(3-hydroxyprop-1-yn-1-yl)phenyl]carbamate 
• 3867-18-3 2-vinylaniline 
• 911022-62-3 N-(methoxycarbonyl)-2'-vinylacetanilide 
• 23206-21-5 methyl 2-vinylaniline-N-carboxylate 
• 911022-76-9 methyl (1-methylethenyl)(2-vinylphenyl)carbamate 

Downstream Products

• 29475-88-5 trans-2-styrylindole 
• 144137-01-9 (1-methoxycarbonylindol-2-yl)methyl(triphenyl)phosphonium bromide 

Relevant academic research and scientific papers

Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles

Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.

Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor

A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and 1H NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl- to form a 1:1 adduct (Ka= 1042 ± 21 in CD3CN). Among alkali metal ions, Li+ and Na+ showed the strongest binding in the formation of a 1·M+ complex. The simultaneous binding of Cl- and Li+ to 1 was confirmed by 1H NMR titration of a 1:1 mixture of 1 and Cl- with LiPF6 in 83:17 v/v mixture of CDCl3 and DMSO-d6. DFT-optimized structures of 1·Cl-, 1·Li+, and 1·Li +·Cl- are consistent with the chemical shift changes observed in 1H NMR studies.

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Intramolecular trapping of allenylzincs by carbonyl groups

Allenylzinc formed via oxygen-promoted zinc/iodine exchange between propargyl iodides and diethylzinc can be trapped by intramolecular reaction with various electrophiles such as aldehydes, ketones, esters, carbamates, and imides. Potentially useful build

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.

Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines

A novel and efficient synthesis of the pyrido[3′,2′:4,5] pyrrolo[1,2-c]pyrimidine system, the heterocyclic core of the variolin family of marine alkaloids, is described. The route involves the reaction of 3-bromo-2-(bromomethyl)pyrrolo[2,3-b]pyridine and tosylmethyl isocyanide (TosMIC) under phase-transfer conditions. This unprecedented reaction was also used to synthesize a series of new methoxycarbonyl azolopyrimidines by reaction of TosMIC with bromomethylindoles, bromomethylbenzimidazole, and bromomethylpyrazole. Hydrolysis and decarboxylation of 5-bromo-7- methoxycarbonylpyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine obtained by this heterocyclization process and installation of the pyrimidine moiety in the C5 position open an alternative approach to complete a total synthesis of variolin B.

A simple synthesis of 2-substituted indoles

A simple preparation of 2-(dimethylaminomethyl)indole, indole-2-acetonitrile and 2-(2-arylvinyl)indoles from 2-methylindole is described.