1402148-99-5

Upstream product

• 114604-96-5 tert-butyl 2-formyl-1H-indole-1-carboxylate 
• 1402148-97-3 C₁₅H₁₆F₃NO₃ 
• 383-63-1 ethyl trifluoroacetate, 
• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 228873-77-6 2,2,2-trifluoro-1-(1H-indol-2-yl)ethan-1-one 

Relevant academic research and scientific papers

Synthesis, Stability, and Photoreactivity of Diazirinyl-Substituted N-Heterocycles Based on Indole, Benzimidazole, and Imidazole

The synthesis, thermal stability, and photoreactivity of trifluoromethyl diazirines installed at the heterocyclic section of N-methylindole, N-methylbenzimidazole, and at N-methylimidazole were investigated. N-Tosyl-3-diazirinylindole and N-methyl-2-diazirinylbenzimidazole proved to be thermally stable, whereas the corresponding 2-diazirinylindole was not. The least stable was 2-diazirinylimidazole, which underwent rapid decomposition. Quenching with ethanol indicated that the corresponding carbene was formed. Decomposition is rationalized by exothermic coarctate ring-opening of the carbene. Quantum mechanical calculations [B3LYP/6-311G(2d,2p)] predict singlet ground states of all carbenes. Accordingly, Friedel-Crafts alkylation products were formed on irradiation (350 nm, Rayonet) of the N-methylbenzimidazole-based diazirine in the presence of phenol.

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K2CO3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o-iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and heteroaryl trifluoromethyl ketones.