Category: 16681-56-4

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., name: 2-Bromo-1H-imidazole

2-Bromo-lH-imidazole (100 mg, 0.680 mmol) was dissolved in DMF (2 mL) in a microwave vial in an ice bath and purged with nitrogen for 10 min. With the solution at 0 C, sodium hydride (60% dispersion in mineral oil) (62.6 mg, 1.565 mmol) was added and the solution was stirred for 10 min under nitrogen. A solution of 2-(bromomethyl)pyridine hydrobromide (207 mg, 0.816 mmol) in DMF (2 mL) was added dropwise to the reaction mixture. Once all reagents were added, the reaction mixture was allowed to warm to RT and stirred for 2 days under an atmosphere of nitrogen. The solvent was removed under reduced pressure. The crude product was dissolved in ethyl acetate (20 mL) and washed with brine (20 mL). The solvent was again removed from the organic layer under reduced pressure. The samples were dissolved in 1: 1 MeOH:DMSO (3 mL) and purified by MDAP (Method B). The solvent was evaporated in vacuo to give the title compound. LCMS (System B): tRET = 0.63 min; MH+ 238, 240.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
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., Quality Control of 2-Bromo-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
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., Formula: C3H3BrN2

CS2CO3 (568 mg, 1.74 mmol) was added to a solution of Cul (16.2 mg, 85.1 pmol) and l,l,l-tris(hydroxymethyl)ethane (10.2 mg, 85.1 iimol) in anhydrous l,4-dioxane (45 mL) and anhydrous DMF (5 mL) in a sealed tube while N2 was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (130 mg, 0.85 mmol) and 2-bromo- lH-imidazole [16681-56-4] (150 mg, 1.02 mmol) were added. The reaction mixture was stirred at room temperature for 10 min, and at 110 C for 4 days. The mixture was filtered through Celite and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 60:40) to afford 1-151 (36 mg, 18%, 35% purity).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-56-4, The chemical industry reduces the impact on the environment during synthesis 16681-56-4, name is 2-Bromo-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step 1. 2-Bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (0910) [00290] A mixture of 2-bromo-lH-imidazole (20 g, 136.99 mmol) and potassium carbonate (56.71 g, 410.97 mmol) in acetone (200 mL) was treated by the dropwise addition of (2- (chloromethoxy)ethyl)trimethylsilane (27.29 g, 164.39 mmol) and the resulting mixture was stirred for 3 h at ambient temperature. The reaction mixture was filtered, concentrated under vacuum and the residue was purified by silica gel chromatography (eluting with a gradient of 1- 10% EtOAc/PE) to afford 30 g (80%) of 2-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazole as a colorless oil. MS (ESI) m/z 277 [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, 2-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16681-56-4 as follows. Computed Properties of C3H3BrN2

Obtained in Example 50 (a) (S) -1-tert- butoxycarbonylamino-4- (5-chloro-7- (4,4,5,5-dioxa -1,3,2- borane-2-yl)benzoxazol-2-yl) -3-methyl piperazine (48 mg, 0.1mmol), 2- bromo -1H- imidazole (29 mg, 2.0 eq.), Tetrakis(triphenylphosphine) palladium (0) (11.6 mg, 0.1 eq), potassium carbonate (55 mg, 4.0 equiv) 1, 4-dioxane (800muL) and water (200muL) for dissolution, and under an argon atmosphere in an oil bath from 110 4 hours with stirring did. Water was added to the reaction mixture, the product extracted with ethyl acetate, an organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by preparative TLC (developing solvent, methanol: chloroform = 1: 19) to give the title compound 21.3 mg.

According to the analysis of related databases, 16681-56-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MeijiSeika Pharma Corporation; Kikuchi, Jika; Tabata, Yuji; Yamakawa, Takeru; Matsuhira, Takashi; Watanabe, Naoko; Kuboda, Natsuki; Kaneda, Kaoru; (143 pag.)KR2016/30503; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To 7.3 g (50 mmol) of 2-bromo-1H-imidazole, 11.1 g of 9-anthracene boronic acid(50 mmol) and 3.5 g (5 mmol) of bistriphenylphosphine palladium dichloride were added 130 ml of 2M aqueous sodium carbonate solution, 260 ml of methylBenzene and 86 ml of ethanol at 100 C for 12 hours. After the system had cooled down, extract with methylene chloride and wash with distilled waterThe organic phase is then washed with anhydrous magnesium sulfate and the solvent is evaporated to dryness. Column chromatography (n-hexane: dichloromethane = 20: 1)Purification gave 8.43 g of intermediate A-1.

The synthetic route of 2-Bromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhou Wenting; Cai Hui; (17 pag.)CN107383071; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 16681-56-4, name is 2-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H3BrN2

To a solution of 2-bromo-1H-imidazole (300.00 mg, 2.04 mmol, 1.00 eq) in THF (5.00 mL) was added batchwise NaH (106.00 mg, 2.65 mmol, 60% purity, 1.30 eq) at 0C. After addition, the mixture was stirred at this temperature 0.5 h, and then 2-(chloromethoxy) ethyltrimethylsilane (442.14 mg, 2.65 mmol, 470.36 uL, 1.30 eq) was added dropwise at 0C. The resulting mixture was stirred at 20C for 15.5 h. It was quenched by addition water 50 mL, and extracted with EtOAc (20 mLx3), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, PE/EtOAc =20/1 to 5:1) to afford the title compound (500.00 mg, 1.80 mmol, 88.41% yield) as a colorless oil.

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

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-56-4, 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.

20 g (0.136 mmol) of 2-bromo-lH-imidazole and 3.9 g (0.163 mmol) of sodium hydride were dissolved in 500 ml of THF in a round-bottomed flask, and the solution was stirred and refluxed under a nitrogen stream for one hour. Then, 40.5 g (0.217 mmol) of 3-(2-bromoethyl)pyridine was added thereto in a dropwise fashion, and the mixture was stirred and refluxed for 3 hours. When the reaction was complete, sodium hydride remaining therein was quenched by methanol. After separating an organic layer and an aqueous layer, a solvent therein was all removed. Subsequently, a resultant therefrom was treated through column chromatography, obtaining 23 g of an intermediate compound-15 (a yield: 67%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEIL INDUSTRIES INC.; KIM, HYUN JUNG; CHAE, MI YOUNG; LEE, NAM HEON; HUH, DAL HO; KIM, WOOK; KIM, YOUN HWAN; KIM, JUN SEOK; LEE, SANG IL; LEE, HYUN GYU; JANG, CHUN KEUN; JUNG, JU YEON; (32 pag.)KR2015/66887; (2015); A;,
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., Product Details of 16681-56-4

A solution of 5,7-dimethyl-N-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)pyrazolo[l,5-a]pyrimidine-3-carboxamide 6 (440 mg, 1.12 mmol) in DMF (5 mL) was charged with 2-bromo-lH- imidazole (150 mg, 1.02 mmol), potassium carbonate (422 mg, 3.06 mmol) and the mixture was degassed with argon for 15 min. To the resulting solution was added Pd(PPh3)4(1 17 mg, 0.10 mmol) and the reaction mixture was degassed for another 10 min and heated at 100C for 15h. Then, the reaction mixture was diluted with water (10 mL), extracted with ethyl acetate (3 X 10 mL) and the combined organic layer was dried over sodium sulphate and concentrated in vacuo to obtain crude compound. The crude compound was purified by FCC (eluent, 1-3% methanol in DCM) to afford the title compound as a white solid (40 mg, 12%). NMR (400 MHz, DMSO-i) delta 12.48 (br s, 1H), 10.27 (s, 1H), 8.65 (s, 1H), 7.93 (d, J=8.87 Hz, 2H), 7.82 (d, J=8.87 Hz, 2H), 7.07-7.24 (m, 3H), 2.78 (s, 3H), 2.73 (s, 3H). ES-MS m/z 333.35 (M+H)+. HPLC purity 98.3%.

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.

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., SDS of cas: 16681-56-4

Example 242 Trans-4-(4-(imidazol-2-yl)-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide Trans-N-((R)-1-(4-fluorophenyl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonamido)cyclohexanecaboxamide (Intermediate 64, 0.206 mmol), Pd(dppf)Cl2.DCM (19 mg, 0.023 mmol), 2M Na2CO3 (0.57 ml, 1.14 mmol) and 2-bromo-imidazole (17 mg, 0.114 mmol) dissolved in DMF (2 ml) under N2, and the mixture was microwaved at 160 C. for 20 min., after which LCMS indicated that the reaction was complete. The mixture was diluted with DCM and MeOH and filtered through a syringe filter. The filtrate was then passed through a 40+S biotage column with an isocratic gradient of 10% MeOH in EtOAc and the product fractions were combined and concentrated. Crude product was repurified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA) and the product containing fractions were lyophilized to yield the title compound as a white solid (4.2 mg, 3%). MS MH+ 471.1

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

Reference:
Patent; BARNES, David; BEBERNITZ, Gregory Raymond; COHEN, Scott Louis; DAMON, Robert Edson; DAY, Robert Francis; JAIN, Monish; KARKI, Rajeshri Ganesh; KIRMAN, Louise Clare; PATEL, Tajesh Jayprakash; RAYMER, Brian Kenneth; SCHUSTER, Herbert Franz; ZHANG, Wei; US2011/136735; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem