With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57319-65-0,6-Aminoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.
57319-65-0, Phthalide 29. To a stirred solution of 6-aminophthalide (10.0 g, 67.0 mmol, 1.0 equiv), DMAP (164 mg, 1.34 mmol, 0.02 equiv), and Et3N (13.6 g, 18.7 mL, 134 mmol, 2.0 equiv) in THF (40 mL) at 0 C, Boc20 (17.6 g, 80.4 mmol, 1.2 equiv) was added portionwise over 10 min under vigorous stirring at 0 C (CA UTION: gas evolution). Upon completion of addition, the ice bath was removed and the reaction mixture was stirred for 3 h at 40 C and was diluted with EtOAc (50 mL), cooled to 0 C, quenched by careful addition of saturated aq. NH4CI (40 mL). The resulting mixture was extracted with EtOAc (3 x 50 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried over MgSC>4 and concentrated. Flash column chromatography (silica gel, hexanes:EtOAc 2: 1 to 1 : 1) gave phthalide 29 as a yellowish solid (13.4 g, 53.6 mmol, 80% yield). 29: R/ = 0.31 (silica gel, hexanes:EtOAc 2: 1); IR (film) vmax = 3341, 2979, 2931, 2851, 1741, 1719, 1604, 1538, 1497, 1450, 1423, 1390, 1365, 1316, 1299, 1234, 1126, 1063, 1002 cm”1; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13): delta = 7.83 (d, J = 2.0, 1 H), 7.76 (d, J = 7.8, 1 H), 7.36 (d, J = 8.3, 1 H), 6.92 (br, 1 H), 5.23 (s, 2 H), 1.47 (s, 9 H) ppm; 1 C NMR (125 MHz, CDC13): delta = 170.9, 152.5, 140.5, 139.6, 126.4, 124.8, 122.5, 114.6, 81.1, 69.5, 28.2 ppm; HRMS (ESI-TOF): calcd for Ci3H16N04+ [M+H+]: 250.1074, found 250.1076.
57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.
Reference£º
Patent; WILLIAM MARSH RICE UNIVERSITY; BRISTOL-MYERS SQUIBB COMPANY; THE SCRIPPS RESEARCH INSTITUTE; NICOLAOU, Kyriacos, C.; LU, Min; MANDAL, Debashis; GANGWAR, Sanjeev; CHOWDARI, Naidu, S.; POUDEL, Yam, B.; WO2015/23879; (2015); A1;,
Benzofuran – Wikipedia
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