193810-79-6

Usage

Studied for its potential pharmacological properties, including

+ Anti-inflammatory
+ Anti-cancer
+ Antimicrobial activities
Used as a precursor in the synthesis of various pharmaceuticals and agrochemicals

Has applications in

+ Organic synthesis
+ Medicinal chemistry
Valuable compound in the field of drug discovery and development

Upstream product

• 948-65-2 2-phenyl-indole 
• 3282-30-2 pivaloyl chloride 
• 70957-04-9 N-pivaloyl indole 
• 71-43-2 benzene 
• 170959-10-1 2-iodo-pivaloylaminobenzene 
• 591-50-4 iodobenzene 
• 120-72-9 indole 
• 536-74-3 phenylacetylene 
• 221353-38-4 N-<2-(2-Phenylethynyl)phenyl>-2,2-dimethylpropanamide 

Downstream Products

• 948-65-2 2-phenyl-indole 

Relevant academic research and scientific papers

Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling

By changing the stoichiometric oxidant and modifying the indole N-substituent in palladium-catalyzed oxidative arene cross-coupling reactions, both C2 and C3 oxidative indole arylation can be achieved in high yield. High regioselectivity can also be achieved with the benzene component, and the use of this methodology with pyrrole substrates is illustrated. A mechanistic hypothesis for the change in C2/C3 selectivity is advanced. Copyright

On water phosphine-free palladium-catalyzed room temperature C-H arylation of indoles

Get on top of your chemistry! An "on water", palladium-catalyzed, phosphine-free direct C-H arylation of indoles, with iodoarenes at 25-30°C, is disclosed (see scheme; TBDMS=N-tert-butyldimethylsilyl ether; SEM=N-2-(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1-protected indoles.

A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles

Two mild and general protocols for the high-yielding deprotection of indoles and related fused heterocyclic systems are described, involving either hydride transfer from LDA or hydrolysis by the DBU-water system. Both methods were shown to tolerate a wide variety of substituents and functional groups, but the hydrolytic one proved to be particularly general, being compatible with 2-alkyl substituents, aldehydes, ketones, carboxylic acids, halogens, ethers, amides and esters. Yields were normally excellent in both cases, but were usually slightly higher for the reductive method. Taken together, these two protocols provide a general solution to the problem of pivaloyindole deprotection.

An efficient procedure for the deprotection of N-pivaloylindoles, carbazoles and β-carbolines with LDA

Treatment of variously substituted indoles with 2 equivalents of LDA at 40-45 °C led to their fast and efficient deprotection. This method was also extended to N-pivaloylcarbazoles and β-carbolines.

Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride

The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.