1076-74-0 Usage
Description
5-METHOXY-2-METHYLINDOLE is an indole derivative, a useful organic raw material with a white to light beige crystalline powder form. It is known for its effective inhibition of the chlorinating activity of myeloperoxidase (MPO) and is utilized in the metabolic synthesis of arylacetic acid anti-inflammatory agents.
Uses
Used in Pharmaceutical Industry:
5-METHOXY-2-METHYLINDOLE is used as a reactant for the preparation of indolylquinoxalines by condensation reactions, which are important in the development of pharmaceutical compounds.
Used in Chemical Synthesis:
5-METHOXY-2-METHYLINDOLE is used as a reactant in the preparation of alkylindoles via Ir-catalyzed reductive alkylation, contributing to the synthesis of various organic compounds.
Used in Catalyst-Mediated Reactions:
5-METHOXY-2-METHYLINDOLE is used as a reactant in arylation reactions using a palladium acetate catalyst, which is crucial for the formation of new carbon-carbon bonds in organic synthesis.
Used in Enantioselective Synthesis:
5-METHOXY-2-METHYLINDOLE is used as a reactant in enantioselective Friedel-Crafts alkylation, a process that allows for the selective synthesis of one enantiomer over another, which is essential in the production of chiral drugs.
Used in Stereoselective Synthesis:
5-METHOXY-2-METHYLINDOLE is used as a reactant in the stereoselective synthesis of cyclopentaindolones via stereoselective [3+2] cyclopentannulation, which is important for the creation of specific stereoisomers with desired biological activities.
Used in Enzyme Inhibition:
5-METHOXY-2-METHYLINDOLE is used as an effective inhibitor of the chlorinating activity of myeloperoxidase (MPO), which has potential applications in the treatment of various diseases associated with MPO overactivity.
Used in Metabolic Synthesis:
5-METHOXY-2-METHYLINDOLE is used in the metabolic synthesis of arylacetic acid anti-inflammatory agents, contributing to the development of new medications for inflammation-related conditions.
References
https://www.alfa.com/en/catalog/B21348/
http://www.sigmaaldrich.com/catalog/product/aldrich/m15451?lang=en®ion=US
https://pubchem.ncbi.nlm.nih.gov/compound/5-Methoxy-2-methylindole#section=2D-Structure
Check Digit Verification of cas no
The CAS Registry Mumber 1076-74-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 6 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1076-74:
(6*1)+(5*0)+(4*7)+(3*6)+(2*7)+(1*4)=70
70 % 10 = 0
So 1076-74-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO/c1-7-5-8-6-9(12-2)3-4-10(8)11-7/h3-6,11H,1-2H3
1076-74-0Relevant articles and documents
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Degutis,Barkauskas
, (1969)
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Welch
, p. 645 (1977)
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Cobalt-Catalyzed Dearomatization of Indoles via Transfer Hydrogenation to Afford Polycyclic Indolines
Chen, Siwei,Cai, Min,Huang, Junru,Yao, Hequan,Lin, Aijun
supporting information, p. 2212 - 2216 (2021/04/05)
A cobalt-catalyzed dearomatization of indoles via transfer hydrogenation with HBpin and H2O has been developed. This reaction offered a straightforward platform to access hexahydropyrido[1,2-a]indoles in high regio- and chemoselectivity. A preliminary reaction mechanism was proposed on the basis of deuterium-labeling experiments, and a cobalt hydride species was involved in the reaction.
Synthesis method for preparing 2-substituted indole derivative
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Paragraph 0235-0241, (2019/05/28)
The invention relates to a synthesis method for preparing a 2-substituted indole derivative. The method includes the following steps: mixing aromatic amine compounds (I), ketone compounds (II) and a drying agent in an organic solvent; adding a palladium catalyst; and reacting in an aerobic weak acid environment to prepare the indole compounds (III). (I), (II) and (III) are as shown in the specification, wherein R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, substituted or unsubstituted amino, substituted or unsubstituted phenyl, pyridyl and heterocyclic aryl; (I) can be pyridylamine, pyrimidylamine, pyridazinam or pyrazinamide which may further be substituted or unsubstituted; and the substituents are selected fromone or more C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkanoyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, hydroxyl, amino; and R2 is selected from C1-C6 alkyl, formate groups or C1-C6 alkylamide groups.
Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Cycloisomerization of o-Allylanilines Using Organic Redox Cocatalyst
Ning, Xiao-Shan,Wang, Mei-Mei,Qu, Jian-Ping,Kang, Yan-Biao
, p. 13523 - 13529 (2018/10/25)
A scalable and practical synthesis of functionalized indoles via Pd-tBuONO cocatalyzed aerobic cycloisomerization of o-allylanilines is reported. Using molecular oxygen as a terminal oxidant, a series of substituted indoles were prepared in moderate to good yields. The avoidance of hazardous oxidants, heavy-metal cocatalysts, and high boiling point solvents such as DMF and DMSO enables this method to be applied in pharmaceutical synthesis. A practical gram-scale synthesis of indomethacin demonstrates its application potential.