61995-52-6

Usage

Uses

Used in Organic Synthesis:
1-Acetyl-5-bromoindole is used as a versatile building block for the synthesis of various bioactive compounds and pharmaceuticals. Its bromo and acetyl functional groups provide a foundation for further chemical modifications and reactions, enabling the creation of a wide range of chemical entities with potential applications in various industries.
Used in Pharmaceutical Research:
1-Acetyl-5-bromoindole is used as a valuable intermediate in the production of pharmaceutical drugs and biologically active molecules. Its unique structure and functional groups make it an essential component in the development of new drugs and therapeutic agents, contributing to advancements in medicine and healthcare.
Used in Cross-Coupling Reactions:
1-Acetyl-5-bromoindole is used as a valuable tool in cross-coupling reactions, a class of chemical reactions that involve the formation of carbon-carbon bonds. Its bromo substituent makes it a suitable candidate for these reactions, allowing for the synthesis of complex organic molecules and the development of new chemical entities.
Used in the Development of New Chemical Entities:
1-Acetyl-5-bromoindole is used as a key component in the development of new chemical entities and drug candidates. Its unique structure and functional groups make it a valuable asset in the design and synthesis of novel compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H8BrNO/c1-7(13)12-5-4-8-6-9(11)2-3-10(8)12/h2-6H,1H3

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 108-05-4 vinyl acetate 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 106698-05-9 1-acetyl-5-bromo-3-hydroxy-2-methoxyindole 
• 106698-05-9 1-acetyl-5-bromo-3-hydroxy-2-methoxyindole 
• 1038998-08-1 1-(5-bromo-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 54470-20-1 C₁₆H₁₂BrNO 
• 576-15-8 N-acetylindole 
• 2050-23-9 diethyl suberate 
• 1365610-78-1 ethyl 4-(1-acetyl-1H-indol-5-yl)butanoate 
• 105-54-4 butanoic acid ethyl ester 
• 1512868-94-8 1-(5-(2-hydroxypropyl)-1H-indol-1-yl)ethanone 
• 766535-96-0 1-acetyl-1H-indole-5-carbonitrile 
• 111083-49-9 1-(5-vinyl-1H-indol-1-yl)ethanone 
• 1403485-77-7 ethyl 3-(1-acetyl-5-bromo-1H-indol-2-yl)propanoate 
• 443311-42-0 C₁₂H₁₄NO₄P 

Relevant academic research and scientific papers

Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates

The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.

Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.

Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3

We report the FeCl3-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air). No functional group is required on the arene nucleophile: one of its C-H bonds is added to the C2=C3 double bond of the indole nucleus in a Friedel-Crafts-type reaction. This dearomatisation process delivered a broad range of C2-arylated indolines.

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.

Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles

A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: Selective synthesis of linear or branched 2-alkylindoles

A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

A trans diacyloxylation of indoles

A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions. The Royal Society of Chemistry 2012.

Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions

We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright

An efficient synthetic method for 2-methoxy-1,2-dihydro-3H-indol-3-ones

An efficient method for synthesis of 2-methoxy-1,2-dihydro-3H-indol-3- ones using two successive oxidations of indoles is described.