With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-25-9,1-Benzothiophene-3-carboxylic acid,as a common compound, the synthetic route is as follows.
While stirring (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]propan-1-ol (0.173 g, 0.552 mmol), 1-benzothiophene-3-carboxylic acid (see Synth. Commun., 15, 711-713 (1984)) (0.10 g, 0.55 mmol) and 1-hydroxybenzotriazole hydrate (85 mg, 0.55 mmol) in acetonitrile (10 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.55 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and passed through silica gel. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diethyl ether-hexane to give the objective substance. white crystal yield 0.204 g, 78% mp 188-189C; 1H-NMR (CDCl3, 200MHz) delta 2.88-3.08 (2H, m), 3.64 (1H, d, J = 3.6 Hz), 4.59-4.72 (1H, m), 5.13 (1H, t, J = 3.2 Hz), 6.04 (1H, d, J = 8.8 Hz), 7.09 (2H, t, ! J = 8.8 Hz), 7.31-7.60 (9H, m), 7.82-7.92 (2H, m); IR (KBr) 3333, 1622, 1537, 1510, 1331, 1159, 1123, 1069, 833, 766 cm-1; Anal. Calcd for C25H19F4NO2S: C, 63.42; H, 4.04; N, 2.96. Found: C, 63.50; H, 4.10; N, 2.90.
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Reference£º
Patent; Takeda Chemical Industries, Ltd.; EP1362846; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem