889868-60-4

Basic information

• Product Name: ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate
• Synonyms: ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate
• CAS NO: 889868-60-4
• Molecular Weight: 315.249
• Mol File: 889868-60-4.mol

Chemical Properties

• CAS DataBase Reference: ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate(889868-60-4)
• EPA Substance Registry System: ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate(889868-60-4)

Safety Data

• Hazardous Substances Data: 889868-60-4(Hazardous Substances Data)

Upstream product

• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 287477-27-4 2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline 
• 201813-43-6 2,2,2-Trifluoro-N-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-acetamide 
• 615-43-0 2-iodophenylamine 
• 541-41-3 chloroformic acid ethyl ester 
• 148564-88-9 2,2,2-trifluoro-N-(2-(3-hydroxyprop-1-ynyl)phenyl)acetamide 

Downstream Products

• 3978-16-3 N-((1H-indol-2-yl)methyl)-N-ethylethanamine 
• 95-20-5 2-methyl-1H-indole 
• 66946-71-2 1-formyl-2-methyl-indole 
• 1186238-69-6 C₂₀H₂₀FN₃O 
• 1186238-74-3 C₁₆H₂₀N₂O 
• 1186238-71-0 C₂₂H₂₅N₃O₂ 

Relevant articles and documents

Sequential alkylation/cyclization/isomerization of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters: A new route to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles

The reaction of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters with ethyl iodoacetate or α-bromoacetophenone in the presence of K 2CO3 in DMSO provides a new simple access to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles.

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.

2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates

The reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates with formate anions in the presence of Pd(PPh3)4 affords 2-alkylindoles in good to excellent yields.

Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate

The palladium-catalyzed reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1- propargyl carbonate with piperazines in the presence of Pd(PPh3) 4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields are also obtained with other secondary amines.