200345-71-7

Basic information

• Product Name: ethyl 6-phenyl-1H-indole-2-carboxylate
• Synonyms: ethyl 6-phenyl-1H-indole-2-carboxylate
• CAS NO: 200345-71-7
• Molecular Weight: 265.312
• Mol File: 200345-71-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl 6-phenyl-1H-indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-phenyl-1H-indole-2-carboxylate(200345-71-7)
• EPA Substance Registry System: ethyl 6-phenyl-1H-indole-2-carboxylate(200345-71-7)

Safety Data

• Hazardous Substances Data: 200345-71-7(Hazardous Substances Data)

Upstream product

• 98-80-6 phenylboronic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 2243-47-2 3-biphenyl amine 
• 3218-36-8 4-Phenylbenzaldehyde 

Downstream Products

• 1419403-48-7 ethyl 6-phenyl-3-(phenyldiazenyl)-1H-indole-2-carboxylate 
• 1419403-57-8 3-methyl-7-phenyl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione 
• 1419403-54-5 ethyl 3-(ethoxycarbonylamino)-6-phenyl-1H-indole-2-carboxylate 

Relevant articles and documents

Carboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling

The cross-dehydrogenative coupling (CDC) reaction is an efficient strategy for indole synthesis. However, most CDC methods require special substrates, and the presence of inherent groups limits the versatility for further transformation. A carboxylic acid-promoted aerobic catalytic system is developed herein for a single-step synthesis of indoles from simple anilines and ketones. This versatile system is featured by the broad substrate scope and the use of ambient oxygen as an oxidant and is convenient and economical for both laboratory and industry applications. The existence of the labile hydrogen at C-3 and the highly transformable carbonyl at C-2 makes the indoles versatile building blocks for organic synthesis in different contexts. Computational studies based on the density functional theory (DFT) suggest that the rate-determining step is carboxylic acid-assisted condensation of the substrates, rather than the functionalization of aryl C-H. Accordingly, a pathway via imine intermediates is deemed to be the preferred mechanism. In contrast to the general deduction, the in situ formed imine, instead of its enamine isomer, is believed to be involved in the first ligand exchange and later carbopalladation of the α-Me, which shed new light on this indolization mechanism.

Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds

A direct oxidative C-H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C-H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated with good to high yields for numerous electron-rich and electron-poor substrates. Further reaction of selected products via Suzuki arylation and deacetylation provides access to highly functionalized indole structures.

Synthesis of (E)-8-(3-chlorostyryl)caffeine analogues leading to 9-deazaxanthine derivatives as dual A2A antagonists/MAO-B inhibitors

A systematic modification of the caffeinyl core and substituents of the reference compound (E)-8-(3-chlorostyryl)caffeine led to the 9-deazaxanthine derivative (E)-6-(4-chlorostyryl)-1,3,5,-trimethyl-1H-pyrrolo[3,2-d]pyrimidine- 2,4-(3H,5H)-dione (17f), w