Reference of 15965-54-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15965-54-5 name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
To 2-chloro-5-methoxy-1H-benzo[djimidazole (13.04 mg, 0.071 mmol) and Intermediate I-i (20 mg, 0.059 mmol) was added toluene (0.75 mL) and EtOH (0.25 mL). The reaction mixture was stirred at room temperature until solids are dissolved, then [1,1 ?-Bis(diphenylphosphino)ferrocenej dichloropalladium (II) complex with dichloromethane (1:1) (5.83 mg, 7.14 imol) was added. The flask was degassed andflushed with argon. Finally sodium carbonate (0.059 mL, 2M, 0.119 mmol) was added dropwise. The reaction vessel was sealed and bubbled with argon for 5 mm, then placed in microwave reactor at 140 C for 30 mm. The reaction mixture was cooled to room temperature and was diluted with EtOAc and water, extracted with EtOAc (3X). The combined organic layer was washed with brine, dried with Mg504 and concentrated. Thecrude sample was purified with a preparative HPLC (method A, 30-100% B in 8 mm.). The desired fractions were placed in a SpeedVac overnight to remove solvent, then lyophilized to give Example 50 (6 mg, 0.016 mmol, 27.5 % yield). ?H NMR (acetonitrile-d3, 400MHz): = 8.77 (br. s., 2H), 7.70 (s, 3H), 7.27-7.39 (m, 1H), 7.05-7.18 (m, 1H), 3.90 (s, 3H), 2.65 ppm (s, 3H). ?9F NMR (acetonitrile-d3, 376MHz):= -76.64 (br. s., 3F), -90.69 ppm (s, 2F). LC-MS: method C, RT = 1.78 mm, MS (ESI) m/z: 357.0 (M+H). Analytical HPLC purity (method A): 98%
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-methoxy-1H-benzo[d]imidazole, and friends who are interested can also refer to it.
Reference:
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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem