Downstream synthetic route of 14618-45-2

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

To a solution of 2,2,2-trifluoro-l-(lH-indol-3-yl)ethanone (0.20 g, 0.938 mmol) in THF (1 mL) in an ice-bath was added sodium borohydride (71.00 mg, 1.877 mmol) under N2. Then boron trifluoride diethyl ether (0.357 mL, 2.815 mmol) was added dropwise. The reaction was let stirred for 2 h while warmed to room temperature. The mixture was poured into a mixture of ice-water and 5% aqueous NaHC03and extracted with ethyl acetate. The combined organics were concentrated. The residue was purified by silica gel column chromatography to give the title compound (90 mg). LCMS m/z = 200.4 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.57 (q, J = 11.1 Hz, 2H), 7.04 (t, J = 7.4 Hz, 1H), 7.12 (t, J = 7.3 Hz, 1H), 7.20 (s, 1H), 7.37 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 7.9 Hz, 1H).

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles