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 stirred solution of t-butylamine (16.4 mL, 157 mmol, 5 eq.), in THF (56 mL) at -78C under nitrogen was added slowly n-BuLi (62.6 mL, 157 mmol, 2.5 M in hexanes, 5 eq.). The solution was stirred at -78 oC for 1 h. To the anion was added a solution of 3-trifluoroacetylindole (6) (6.67 g, 31.3 mmol, 1 eq.) in THF (50 mL) at 0 C. The reaction mixture was allowed to gradually warm to rt over 12 h. This was poured onto ice H2O (100 mL) and stirred for 2 h before the aqueous solution was extracted with CH2Cl2 (1 x 65 mL). The entire solution was filtered through Celite to separate the emulsion that formed. The aqueous layer was further extracted with CH2Cl2 (3 x 65 mL). The organic layers were combined, washed with brine (1 x 100 mL), dried (Na2SO4), and concentrated in vacuo to give a dark yellow oil. The oil was purified by flash chromatography (2:1 hexanes: EtOAc) to give 9 as a pale yellow solid (6.76 g, 79%): 1H-NMR (CDCl3) 9.60 (s, 1H), 7.89-7.85 (m, 1H), 7.68 (d, 1H, J 2.8 Hz), 7.41-742 (m, 1H), 7.26-7.21 (m, 2H), 5.94 (s, 1H), 1.55 (s, 9H); 13C-NMR (CDCl3) 165.5, 136.7, 128.5, 124.3, 122.5, 121.3, 119.1, 113.0, 112.5, 51.5, 29.3; IR (film) 3399, 3231, 2964, 1627, 1538, 1449, 1231, 737 cm-1; MS m/z 216 (M+), 161, 144, 116, 89. An analytical sample was obtained via iterative recrystallizations from Et2O: mp 188-190 C. Anal. Calcd for C13H16N2O: C, 72.19; H, 7.46; N, 12.95. Found: C, 72.14; H, 7.41; N, 12.87., 14618-45-2
As the paragraph descriping shows that 14618-45-2 is playing an increasingly important role.
Reference：
Article; Badenock, Jeanese C.; Fraser, Heidi L.; Gribble, Gordon W.; Arkivoc; vol. 2018; 5; (2018); p. 140 – 149;,
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