16382-15-3 Usage
Description
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE, also known as 5-Methylindole-2-carboxylic acid ethyl ester, is an indole derivative that serves as a crucial building block or intermediate in the synthesis of various pharmaceutical agents. Its indole ring system is formed during the Fischer indolization of ethyl pyruvate 2-[2-(methanesulfonyloxy)-4-methyl]phenylhydrazine.
Uses
Used in Pharmaceutical Synthesis:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for the synthesis of oxazino[4,3-a]indoles via cascade addition-cyclization reactions. This application is crucial for the development of novel pharmaceutical compounds with potential therapeutic properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for the preparation of indolecarboxamides, which act as cannabinoid CB1 receptor antagonists. These antagonists have potential applications in the treatment of various disorders related to the cannabinoid system.
Used in Anti-inflammatory and Analgesic Drug Development:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is also utilized as a reactant for the preparation of indole-3-propionic acids, which possess anti-inflammatory and analgesic properties. These agents can be used in the development of drugs for the treatment of pain and inflammation.
Used in Organic Chemistry:
In organic chemistry, ETHYL 5-METHYLINDOLE-2-CARBOXYLATE serves as a reactant for Friedel-Crafts acylation with nitrobenzoyl chloride. This reaction is an important synthetic method for the formation of carbon-carbon bonds and the synthesis of various organic compounds.
Used in Oximation Reactions:
ETHYL 5-METHYLINDOLE-2-CARBOXYLATE is used as a reactant for oximation reactions, which are significant in the synthesis of complex organic molecules and the development of new chemical entities with potential applications in various industries.
Check Digit Verification of cas no
The CAS Registry Mumber 16382-15-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,3,8 and 2 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 16382-15:
(7*1)+(6*6)+(5*3)+(4*8)+(3*2)+(2*1)+(1*5)=103
103 % 10 = 3
So 16382-15-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H13NO2/c1-3-15-12(14)11-7-9-6-8(2)4-5-10(9)13-11/h4-7,13H,3H2,1-2H3
16382-15-3Relevant articles and documents
Fischer indolization and its related compounds. XIII. Measurement of the nuclear magnetic resonance spectra of ethyl indole-2-carboxylate derivatives using the shift reagent and its application
Ishii,Murakami
, p. 413 - 420,414, 418 (1979)
-
Synthesis method for preparing 2-substituted indole derivative
-
Paragraph 0055-0058, (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.
Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles
Xie, Hui,Yang, Jian-Xin,Bora, Pranjal Protim,Kang, Qiang
, p. 3014 - 3021 (2016/05/19)
A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.
