58246-80-3

Usage

Uses

Used in Medicinal Chemistry:
1-Acetyl-5-methoxyindole is used as a building block for the synthesis of various biologically active molecules, which is crucial in the development of new drugs and pharmaceutical compounds. Its structural features and reactivity make it a versatile component in the creation of potential therapeutic agents.
Used in Pharmaceutical Industries:
1-Acetyl-5-methoxyindole is utilized as a key intermediate in the production of pharmaceuticals, particularly in the synthesis of drugs that target specific biological pathways or receptors. Its presence in drug molecules can influence the overall efficacy, potency, and selectivity of the final drug product.
Used in Chemical Synthesis:
1-Acetyl-5-methoxyindole is employed as a reagent in the synthesis of complex organic compounds, where its functional groups can be manipulated to produce a wide range of chemical products. This versatility is essential in the development of novel materials and compounds with potential applications in various industries.

InChI:InChI=1/C11H11NO2/c1-8(13)12-6-5-9-7-10(14-2)3-4-11(9)12/h3-7H,1-2H3

Upstream product

• 1006-94-6 5-methoxylindole 
• 108-24-7 acetic anhydride 
• 4770-33-6 1-acetyl-2,3-dihydro-5-methoxy-1H-indole 
• 78827-74-4 7-Methoxy-2-methyl-benzo[d][1,3]diazepine-3-carboxylic acid ethyl ester 
• 78827-69-7 C₁₄H₁₆N₂O₃ 
• 74054-28-7 N-(2-bromo-5-methoxyphenethyl)acetamide 
• 108-05-4 vinyl acetate 
• 872-36-6 vinylene carbonate 
• 51-66-1 4-methoxyacetanilide 
• 90271-35-5 2-amino-5-methoxy-benzaldehyde-oxime 
• 36688-73-0 N-(3-methoxyphenylethyl)acetamide 
• 79069-37-7 1-(acetamino)-2-bromo-4-methoxybenzene 
• 84689-22-5 2,4,6-Trimethyl-benzenesulfonate1-amino-6-methoxy-2-methyl-quinolinium; 
• 1078-28-0 6-methoxyquinaldine 

Downstream Products

• 1006-94-6 5-methoxylindole 
• 942924-10-9 1-(5-methoxy-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 1235306-53-2 2-(2',4'-dimethoxyphenyl)-5-methoxy-N-acetylindole 
• 54888-61-8 5-methoxy-2-phenyl-2,3-dihydro-indole 
• 1224728-83-9 C₁₈H₁₇NO₃ 
• 942924-01-8 1-(5-methoxy-3-phenyl-1H-indol-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Formation of 3H-1,3-Benzodiazepines from Quinoline N-Acylimides

Photolysis of the quinoline N-imides (3) having an electron-donating substituent in the 6- or 8-position affords the corresponding 3H-1,3-benzodiazepines (4), whereas quinolines having an electron-donating group in the other positions or an electron-withd

Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate

Transition-metal-catalyzed C-H activation and subsequent oxidative cyclization with alkynes has been a powerful tool for the synthesis of polycyclic aromatic compounds. Despite the substantial progress in this field, it is still a significant challenge to establish synthetic methodologies for the construction of nonsubstituted vinylene-fused aromatics. We herein report a Rh(III)-catalyzed C-H/N-H annulation with vinylene carbonate as an acetylene surrogate. Vinylene carbonate also acts as an internal oxidant to regenerate the Rh(III) species in situ; thus, no external oxidant is required to trigger the oxidative annulation. This protocol is applicable to the direct synthesis of various N-heteroaromatics.

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.

Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid

An unusual transformation of indoles to pyrazoles via an aromatic ring-opening strategy has been developed. The salient feature of this strategy involves the C2-N1 bond opening and concomitant cyclization reaction of the C2=C3 bond of the indole moiety with the tosylhydrazone, which proceeds under transition-metal and ligand free conditions. This ring-opening functionalization of indoles provides a wide scope of differently substituted pyrazoles.

Based on carboxylic acid allyl ester as the acylation reagent N - acyl indoles preparation method (by machine translation)

Based on carboxylic acid allyl ester as the acylation reagent N - acyl indoles preparation method, which belongs to the medical and chemical intermediates and related chemical technical field. This method uses the indole compounds and carboxylic acid allyl ester as the raw material, in the catalysis of alkali, realizes the N - acyl indoles of green, efficient synthesis. The method has high selectivity, mild reaction conditions, functional group compatibility is good, wide substrate range, environment-friendly and the like. Because the N - acyl indoles is an important organic synthetic intermediates, in organic synthesis and in the field of pharmacy has very wide application, therefore, the invention has great application value and social and economic benefits. (by machine translation)

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.

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.

A simple, effective, green method for the regioselective 3-acylation of unprotected indoles

A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.

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.

Oxaziridine-mediated oxyamination of indoles: An approach to 3-aminoindoles and enantiomerically enriched 3-aminopyrroloindolines

A radical solution: A highly regioselective copper(II)-catalyzed oxyamination of N-acyl indoles with oxaziridines gave aminal products that could be converted in a single step into 3-aminoindoles and 3-aminopyrroloindolines (see scheme). When a chiral N-acyl group was used, the core fragment of some architecturally fascinating pyrroloindoline alkaloids was formed with 91% ee. Bs=benzenesulfonyl, Moc=methoxycarbonyl. Copyright