Category: 16681-56-4

Some common heterocyclic compound, 16681-56-4, name is 2-Bromo-1H-imidazole, molecular formula is C3H3BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C3H3BrN2

In a 10 mL vial was combined N-(4-fluoro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.30 g, 0.65 mmol), 2-bromo-1H-imidazole (0.143 g, 0.97 mmol), and KOAc (0.159 g, 1.62 mmol) in dioxane (3 mL) to give a black suspension. Nitrogen gas was bubbled in for 20 min before Pd(PPh3)4 (0.075 g,0.06 mmol) was added. The reaction was heated under microwave at 130 C for 4h. After concentration under reduced pressure the residue was dissolved with DMSO (0.5 mL) and MeOH (1.5 mL), filtered and purified by Gilson HPLC (MeCN/0.1% TFA in water) to give the title compound (2 M HCl in Et2O was added) as the HCl salt (0.050 g, 19% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-56-4, its application will become more common.

Reference:
Article; Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.; Bioorganic and Medicinal Chemistry; vol. 28; 2; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16681-56-4

To a microwave vial was added 6-(2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-5 dioxaborolan-2-yl)phenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine(Intermediate 9-3, 100 mg, 0.21 mmol), 2-bromo-1 H-imidazole (61.2 mg, 0.42 mmol), Na2C03 (44mg, 0.42 mmol), and Pd(PPh3)2CI2 (14 mg, 0.02 mmol), followed by DME (1 mL)/EtOH 0.25ml)/(H20 (0.25 ml). The vial was purged with N2 for 10 min and the reaction mixture was heated at150C in a microwave reactor for 20 min. The reaction mixture was filtered through celite and the10 filter cake was washed with EtOAc. The filtrate was concentrated in vacuo to give the crude productwhich was purified by silica gel chromatography (5%-15% MeOH/DCM) to afford 6-(4-(1 H-imidazol-2-yl)-2-methoxyphenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (40 mg,MS: 421.3 [M+H+]).

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEUNG, Atwood; CHIN, Donovan Noel; DALES, Natalie; FAZAL, Aleem; HURLEY, Timothy Brian; KERRIGAN, John; O’BRIEN, Gary; SHU, Lei; SUN, Robert; SUNG, Moo; WO2014/28459; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16681-56-4, name is 2-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H3BrN2

I -((2S,3R,4R)-2-cyclopropyl-3-methyl-4-(pyrimidin-2-ylamino)-6-(4 ,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-3,4-dihydroq uinolin- I (2H)-yl)ethanone (for a preparation see Intermediate 388, 51mg, 0.114 mmol), 2-bromo-IH-imidazole (33.4 mg, 0.227 mmol), potassium carbonate (47.2 mg,0.341 mmol) and PdCI2(PPh3)2 (15.97 mg, 0.023 mmol) were combined in a mixture of I ,4-dioxane(2 mL) and water (0.667 mL) and heated in the microwave reactor at 120 C for I h. The reactionmixture was diluted with EtOAc (25 mL) and water (25 mL). The mixture was run through a 2.5 gcelite cartridge and the layers were separated. The aqueous phase was washed with EtOAc (2x25mL). The organic extracts were dried by passing through a hydrophobic frit and the solvent evaporated in vacuo to give the crude (86 mg). Purification was undertaken by flash column chromatograhpy. The crude material was loaded onto a 10 g silica column and eluted using a graduating solvent system of 0-15% methanol in DCM. Appropriate fractions were combined and thesolvent removed in vacuo to give the product (15.5 mg) as a clear oil.LCMS (2 mm Formic): Rt = 0.56 mi [MH] = 389.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16681-56-4.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16681-56-4, name is 2-Bromo-1H-imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16681-56-4, Formula: C3H3BrN2

Intermediate 124 (150 mg, 0.25 mmol), 2-bromoimidazole (46 mg, 0.31 mmol) andsodium carbonate (79 mg, 0.75 mmol) were suspended in 1 ,4-dioxane (3 mL) andwater (0.25 mL). The reaction mixture was degassed with argon (5 minutes), Pd(PPh3)4 (29 mg, 0.025 mmol) was added and the reaction mixture was heated at 110 C for 12 h in a microwave reactor. The cooled reaction mixture was filtered through celite, washed with EtOAc, then DCM and the filtrate was evaporated in vacuo. The crudematerial was dissolved in THF (4 mL) and TBAF (1M in THF) (1 mL) and heated to40 C for 2 hours. The reaction mixture was concentrated in vacuo and purified bypreparative chromatography using acidic eluent. The material was retrieved andpurified by preparative chromatography using basic eluent to give 6.2 mg of compound163 (6% yield, pale yellow amorphous solid).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HYND, George; MACLEOD, Calum; MANN, Samuel, Edward; KULAGOWSKI, Janusz, Jozef; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; PONCELET, Virginie, Sophie; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; (290 pag.)WO2019/8011; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem