155335-07-2

Upstream product

• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 74-99-7 prop-1-yne 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 5782-14-9 2-methyl-3-(4-methoxybenzene)-1H-indole 
• 26211-90-5 2-methyl-3-(4-methoxybenzoyl)indole 

Relevant academic research and scientific papers

Ni-Catalyzed Reductive Coupling of Alkynes and Amides to Access Multi-Functionalized Indoles

A nickel-catalyzed reductive coupling of alkynes and amides, followed by base-free transmetalation, proceeded selectively in the presence of an uncommon bidentate primary aminophosphine ligand to access highly functionalized indoles comprising biologically important trifluoromethyl groups and challenging electron-rich alkenyl groups at the 2-and 3-positions, respectively. Indole molecules were installed within natural products or drug molecules under mild conditions, and a trifluoromethylated analogue of a drug molecule (pravadoline) was also synthesized.

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.