Related Products of 15965-57-8, 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. 15965-57-8 name is 2-Chloro-7-methyl-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-7-methyl-1H-benzo[d]imidazole (0.65 g, 3.9 mmol) from example 10, step A, in THF (35 mL) was added n-butyllithium (1.6 mL, 3.9 mmol) dropwise at -78C. After 45 minutes, a solution of racemic (1′-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-1′-yl-4-ium)trihydroborate (0.66 g, 4.29 mmol) from the reference example, in THF (10 mL) was added dropwise at -78C. The cooling bath ws removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgSO4, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield racemic (8-methyl-3H-1′-azaspiro[benzo[4,5]imidazo[2,1-b]oxazole-2,3′-bicyclo[2.2.2]octan]-1′-yl-10-ium)trihydroborate (0.40 g, 1.4 mmol, 52%). The 5-methyl regioisomer product was not observed. MS (LC/MS) R.T. = 1.90; [M+1-BH3]+ = 270.07.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-7-methyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.
Reference:
Article; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Fang, Haiquan; Pearce, Bradley; Park, Hyunsoo; Gallagher, Lizbeth; McDonald, Ivar M.; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5002 – 5005;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem