With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.
To 5-methoxybenzofuran (188 mg, 1.269 mmol) in THF (4.0 mL) at -78 C wasadded 1.6 N n-BuLi in hexanes (1.190 mL, 1.903 mmol) dropwise. The solution became slightly yellow. The reaction mixture was stirred at -78 C for 20 mm, followed by addition of triisopropyl borate (0.737 mL, 3.17 mmol). After 30 mm stirring at -78 C, the cooling bath was removed and the stirring was continued at room temperature for 1.5h. The reaction mixture was diluted with EtOAc, quenched with 3.0 mL of 1.0 N HC1.After stirring at room temperature for 25 mm, the organic layer was collected, washedwith brine and dried over sodium sulfate. After evaporation of solvent, the cmde product was dissolved in a small amount of chloroform/a drop of MeOH and charged to a 4 g silica gel cartridge which was eluted with hexanes for 2 mm., then a 10 mm gradient from 0% to 60%. The desired fractions were combined, concentrated and lyophilized to giveIntermediate 2A (170 mg, 0.886 mmol, 69.8 % yield) as a white solid. ?H NMR (500MHz, methanol-d4) oe 7.41 (d, J=9. 1 Hz, 1H), 7.30 (s, 1H), 7.14 (d, J2.5 Hz, 1H), 6.96 (dd, J=8.9, 2.6 Hz, 1H), 3.84 (s, 3H); LC-MS: method A, RT = 1.45 mm, MS (ESI) m/z: 149.0 (M-B(OH)2)t
As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem