143360-93-4

Basic information

• Product Name: AcetaMide, N-(2-ethynylphenyl)-2,2,2-trifluoro-
• Synonyms: AcetaMide, N-(2-ethynylphenyl)-2,2,2-trifluoro-
• CAS NO: 143360-93-4
• Molecular Formula: C₁₀H₆F₃NO
• Molecular Weight: 213.1559496
• Mol File: 143360-93-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: AcetaMide, N-(2-ethynylphenyl)-2,2,2-trifluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: AcetaMide, N-(2-ethynylphenyl)-2,2,2-trifluoro-(143360-93-4)
• EPA Substance Registry System: AcetaMide, N-(2-ethynylphenyl)-2,2,2-trifluoro-(143360-93-4)

Safety Data

• Hazardous Substances Data: 143360-93-4(Hazardous Substances Data)

Upstream product

• 52670-38-9 2-ethynylaniline 
• 407-25-0 trifluoroacetic anhydride 
• 615-43-0 2-iodophenylamine 
• 1066-54-2 trimethylsilylacetylene 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 
• 62236-80-0 3-(4-chlorophenyl)-1H-indole 
• 101125-32-0 3-(4-fluorophenyl)-1H-indole 
• 201813-48-1 N-{2-[(4-acetylphenyl)ethynyl]phenyl}-2,2,2-trifluoroacetamide 
• 30015-86-2 3-(4-methylphenyl)-1H-indole 
• 5782-23-0 3-(4-methoxy-phenyl)-1H-indole 
• 120-72-9 indole 
• 948-65-2 2-phenyl-indole 
• 13141-38-3 2-phenylethynylaniline 
• 1403495-29-3 2,3-bis(4-bromophenyl)-1H-indole 
• 628320-79-6 2,3-bis(4-fluorophenyl)-1H-indole 

Relevant articles and documents

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.

Solid-phase syntheses of furopyridine and furoquinoline systems

Syntheses of 2-substituted furo[3,2-b]pyridines and furo[3,2-h]quinolines have been achieved for the first time in the solid-phase mode. The central enabling steps involved concomitant deprotection/cyclization promoted by the mild base K2COsub

Investigation of the intermolecular Pauson-Khand reaction of various 1-alkynes with cyclic exo-methylene compounds

Intermolecular Pauson-Khand reaction of various 1-alkynes with 4-exo-methylenepiperidine and -cyclohexane derivatives to give corresponding spirocyclopentenones was investigated. The reaction of m- and p-substituted arylalkynes furnished corresponding spirocyclic compounds in good yields, while that of o-substituted arylalkynes and 1-hexyne proceeded in nil to moderate yield.

Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]furans and 2-substituted-indoles

A solventless, microwave-enhanced Sonogashira coupling reaction of aromatic iodides with terminal alkynes on potassium fluoride doped alumina in the presence of palladium powder, cuprous iodide, and triphenylphosphine has been developed. The reaction can be utilized to prepare aryl alkynes in excellent yields. The coupling of o-iodophenol with terminal alkynes leads to the formation 2-substituted-benzo[b]furans. Whereas the coupling of o-iodoanilines with terminal alkynes generates indole products. An in situ desilylation reaction was also developed.

C(2)-(α-Mannosyl)indole: The pivotal intermediate towards the natural C-Glycopeptides

Two different approaches were investigated to prepare the unusual modified peptide C(2)-mannosylated indole residue. Direct glycosylation of 2-metallated indoles or 2-trimethylsilylindole derivative by reaction with perbenzylated α-D-mannopyranosyl bromid

2-Substituted-3-acylindoles through the palladium-catalysed carbonylative cyclization of 2-alkynyltrifluoroacetanilides with aryl halides and vinyl triflates

The palladium-catalysed reaction of readily accessible 2- alkynyltrifluoroacetanilides with aryl halides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) and in the presence of potassium carbonate produces 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.

An efficient synthesis of α-carboline-3-carboxylic acid, ethyl ester (α-CCE)

The use of the Intramolecular Inverse Electron Demand Diels-Alder reaction between an acetylenic dienophile and a pyrimidine diene component is described in the synthesis of α-CCE.

A versatile approach to 2,3-disubstituted indoles through the palladium-catalysed cyclization of oalkynyltrifluoroacetanilides with vinyl triflates and aryl halides

The palladium-catalysed cyclization of o-alkynyltrifluoroacetanilides with vinyl triflates and aryl halides produces 2,3-disubstituted indoles in good to high yield.