With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10242-10-1,5-Chlorobenzofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.
To a solution of N-(l-aminopiperidin-4-yl)-2-(4-chloro-3-fluorophenoxy) acetamide (0.100 g, 0.33 mmol, 1.0 equiv) in DMF (5 mL) was added 5-chlorobenzofuran-2-carboxylic acid (0.065 g, 0.33 mmol, 1.0 equiv) and HATU (0.250 g, 0.66 mmol, 2.0 equiv) at RT. The resulting reaction mixture was stirred for 10 minutes DIPEA (0.28 mL, 0.99 mmol, 3.0 equiv) was added. The reaction mixture was allowed to stir at RT overnight. Product formation was confirmed by LCMS. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (50 mL x 2). Combined organic layer was washed with water (20 mL x 4), dried over anhydrous NaaSOr and concentrated. The crude product was purified by reverse phase HPLC to obtain 5-chloro-N-(4-(2-(4-chloro-3-fluorophenoxy)acetamido)piperidin-l- yl)benzofuran-2-carboxamide (Compound 2 – 20 mg, 12 % yield) as an off white solid. LCMS 480 i H | +; H NMR (400MHz, DMSG-de) d 9 79 (s, 1 H), 8.08 (d, J= 7.5 Hz, 1 H), 7.86 (s, 1 H), 7.70 (d, J= 9.2 Hz, 1 H), 7.54 – 7.38 (m, 3 H), 7.08 (d, J= 8 8 Hz, 1 H), 6.86 (d, .7= 11.8 Hz, 1 H), 4.53 (s, 2 H), 3.66 (br. s., I H), 2.99 (br. s., 2 H), 2.78 (br. s, 2 H), 1.75 (br. s., 2 H), 1.66 (br. s., 2 H)
10242-10-1, 10242-10-1 5-Chlorobenzofuran-2-carboxylic acid 937838, abenzofuran compound, is more and more widely used in various fields.
Reference£º
Patent; PRAXIS BIOTECH LLC; DELGADO OYARZO, Luz Marina; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; (0 pag.)WO2019/236710; (2019); A1;,
Benzofuran – Wikipedia
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