Reference of 24134-09-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
n-BuLi (1.23 M in hexanes, 18.9 mL, 23.2 mmol) was added dropwise to a stirred slurry of 5-bromo-1,2-dimethyl-1H-imidazole (5.13 g, 27.8 mmol) in THF (40 mL) at -78 C. under nitrogen. After stirring for 20 minutes, the slurry was treated dropwise over 2 minutes with a solution of methyl 3-(benzyloxy)-4-chloro-2-methoxyquinoline-6-carboxylate (3.32 g, 9.28 mmol, Intermediate 32) in THF (20 mL). The flask was then rinsed with THF (10 mL), and that was added to the imidazole flask. The reaction was stirred in the dry ice/acetone bath for 10 minutes, then removed from the cold bath and stirred for 20 minutes, then stirred in an ice bath for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl and concentrated to remove the THF. The aqueous residue was partitioned between water (300 mL) and DCM (250 mL). The layers were separated and the aqueous layer further extracted with DCM (250 mL). The organics were combined, dried (Na2SO4), filtered and concentrated to dryness to provide an orange oil. The crude material was purified by FCC (0-10% MeOH/DCM) to afford the title compound as a yellow solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.13 (s, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.58-7.55 (m, 2H), 7.42-7.34 (m, 4H), 6.20 (s, 2H), 5.20 (s, 2H), 4.62 (s, 1H), 4.16 (s, 3H), 3.42 (s, 6H), 2.32 (s, 6H). MS (ESI): mass calcd. for C28H28ClN5O3, 517.2. m/z found, 518.1 [M+H]+.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromo-1,2-dimethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Imidazole – Wikipedia,
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