With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1912-33-0,Methyl 2-(1H-indol-3-yl)acetate,as a common compound, the synthetic route is as follows.
1-Methoxycarbonyl-3-indoleacetic acid methyl ester Methyl indole-3-acetate (2.00 g, 10.57 mmol) was dissolved in dichloromethane (30 ml). To this solution, tetrabutylammonium iodide (TBAI, 30.0 mg, 0.081 mmol) and a 30% aqueous sodium hydroxide solution (24 ml) were added, and the mixture was cooled to 0 C. To the reaction solution, methyl formate chloride (1.96 g, 20.73 mmol) was added, and the mixture was stirred at 0 C. for 2 hours. After the reaction was confirmed by TLC to be complete, the reaction was quenched by the addition of 6 N hydrochloric acid. Water (50 ml) was added thereto, followed by extraction with chloroform (50 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain methyl N-methoxycarbonylindole-3-acetate (2.26 g, yield: 87%): 1H NMR (400 MHz, CDCl3): delta 8.18 (d, J=7.0 Hz, 1H), 7.59 (s, 1H), 7.53 (d, J=7.7 Hz, 1H), 7.35 (t, J=7.5 Hz, 1H), 7.27 (t, J=7.4 Hz, 1H), 4.00 (s, 3H), 3.72 (s, 3H), 3.71 (s, 2H); 13C NMR (100 MHz, CDCl3): delta 171.1, 151.1, 135.2, 129.9, 124.6, 123.8, 122.8, 118.9, 115.0, 113.8, 53.5, 51.9, 30.6; IR (neat): 1746, 1455, 1382, 1258, 1164, 1089, 1018 cm-1; EI-MS: m/z [M]+ 247.
1912-33-0, 1912-33-0 Methyl 2-(1H-indol-3-yl)acetate 74706, aindole-building-block compound, is more and more widely used in various fields.
Reference£º
Patent; TOHOKU UNIVERSITY; KAKE EDUCATIONAL INSTITUTION; KANAGAWA PREFECTURAL HOSPITAL ORGANIZATION KANAGAWA CHILRDEN’S MEDICAL CENTER; ABE, Takaaki; TOMINAGA, Teiji; HAYASHI, Kenichiro; OSAKA, Hitoshi; US2015/353489; (2015); A1;,
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