Category: imidazoles-derivatives

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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-1-methyl-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

Application of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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.

To a suspension of NaOH (0.6 g, 15.4 mmol) inwater (1 mL) at 0 C was added 7 (3.3 g, 7.7 mmol) as a solution indichloromethane (10 mL) and the mixture was stirred for 40 min.The intermediate 6 (3.2 g, 7.7 mmol) was added as a solution indichloromethane (10 mL) drop wise over a period of 3 min. Thereaction was allowed to room temperature and stirred overnight.The mixture was diluted with water and was extracted withdichloromethane to afford the crude product which was purified byflash column chromatography on silica gel to yield 8 as a faintyellow solid (2.9 g, 77.5%). Mp 110e112 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 8.17 (d, J 15.9 Hz, 1H), 7.77 (dd, J 7.8,1.4 Hz, 1H), 7.61e7.51 (m, 3H), 7.45e7.33 (m, 14H), 7.21 (td, J 7.2,6.6, 4.1 Hz, 8H), 7.06e6.89 (m, 2H), 6.32 (d, J 15.9 Hz, 1H), 4.23 (q,J 7.1 Hz, 2H), 4.07 (q, J 7.1 Hz, 1H), 1.29e1.24 (m, 3H), 1.15 (t,J 7.1 Hz, 1H). MS (EI) m/z 485.3 [MH].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-38-6, The chemical industry reduces the impact on the environment during synthesis 3034-38-6, name is 5-Nitro-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-nitro-1H- imidazole (260 mg, 2.299 mmol) in DMF (5 mL) was added 1.0 M NaHMDS/THF (2.53 mL, 2.53 mmol) dropwise at rt. After stirring at rt for 20 min, 1-bromopropan-2-one (315 mg, 2.299 mmol) was added very slowly. The mixture was stirred at rt for ON. Water was added and extracted with EtOAc (4 x 50 mL). The organic layer was concentrated. The residue was purified via silica gel chromatography (12g, DCM-10%MeOH) to give 1-(4-nitro-1H-imidazol-1-yl)propan-2-one (180 mg, 1.064 mmol, 46 % yield). (2333) MS ESI m/z 170.0 (M+H)+ (2334) 1H NMR (499 MHz, CD3OD) delta 8.06 – 8.04 (m, 1H), 7.66 – 7.62 (m, 1H), 5.17 – 5.12 (m, 1H), 2.28 (s, 3H).

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-Nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1072-62-4, 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. 1072-62-4, name is 2-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The synthetic route is shown in Scheme 2. For example, to a stirred solution of compound 2 (506mg, 83 1 mmol) in 30 mL acetonitrile were added anhydrous K2CO3 (275 mg, 2mmol) and imidazole (204mg, 3mmol) at 25. Then the mixture was stirred at 25 for 24 h. The reaction mixture was filtered, and the 85 filtrate was evaporated under reduced pressure. The residue was treated with water (50 mL) and extracted 86 with dichloromethane (4×30 mL). The organic layer was combined, dried with anhydrous Na2SO4, and 87 concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography 88 with chloroform/methanol (5:1) as eluent to give compounds 6-24 as solid.compound 6. 4?-(3-Imidazole-propoxy)-arctigenin. Yeild 83.33%.

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

Reference:
Article; Hu, Yang; Liu, Lei; Li, Boyang; Shen, Yufeng; Wang, Gao-Xue; Zhu, Bin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 183 – 194;,
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. 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Nitro-1H-benzo[d]imidazol-2(3H)-one

Intermediate 301 was prepared from 5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one 10 (CAS: 984-5) and bromoacetamide (CAS: 683-57-8) by the method indicated in the scheme below:

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 93-84-5.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H-Imidazole

To a mixture of toluene and imidazole was added triethyl amine followed by chloroacetonitrile.The reaction mixture was heated and maintained for 7 to 8 hrs. The reaction mass was cooledand the toluene layer was separated. To the reaction mass methylene dichloride was added, stined and filtered. The filtrate was distilled under vacuum. To the residue tetrahydrofuran was added and the reaction mixture is further distilled to obtain the title product. The product thus obtained was recrystallized in isopropyl alcohol. HPLC purity> 99.0 % Chiral purity>99.0%

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; BHUSHAN, Kumar Hari; ZHOPE, Sunil Sudhakar; GHADIGAONKAR, Shailesh Govind; SINGH, Pardeep; DESHMUKH, Shekhar Ashok; CHAND, Prem; (35 pag.)WO2016/92478; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1003-21-0, 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 1003-21-0 as follows.

lntermediate 1: step b (1-Methyl-lH-imidazol-5-yl)(tetrahydro-2H-pyran-4-yl)methanone A clear colorless solution of 5-bromo-l-methyl-lH-imidazole (1.12 g, 6.93 mmol) in THF (10 mL) was placed in an ice bath and ethylmagnesium bromide (3.0 M in Et20, 2.31 mL, 6.93 mmol) was added via syringe. The reaction mixture was stirred for 20 minutes at room temperature. N-Methoxy~N-methyltetrahydro-2H~pyran-4~ca.rboxamide (1.0 g, 5.8 mmol. Intermediate 1 : step a. Procedure A) was added neat by syringe (using 1 mL THF rinse to quantitate transfer), and the resulting white suspension was stirred at room temperature for 2 days. The mixture was diluted with saturated aqueous NH4C1 followed by water, then was extracted with EtOAc (3 x). The organic phase was dried (Na2S04), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography two times (1 -4% MeOH-DCM first column; 40-60% CH CN-DCM second column) to provide the title compound as a white crystalline solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate I-3 4.23 g (11.0 mmol), Intermediate I-4 3.49 g (10.0 mmol), Pd (PPh3) 4 0.06 g (0.5 mmol) and K2CO34.15 g (30.0 mmol) of THF/H2O (2/1 volume ratio) mixed solution and then dissolved in 40 mL, was stirred at 80 for 5 hours. after cooling to room temperature the reaction solution was added to 40 mL water and extracted three times with diethyl ether, 50 mL. The combined organic layers were dried over magnesium sulfate, and separation of the residue obtained by evaporation of the solvent by silica jelgwan chromatography to give the compound 4 4.33 g (yield 81%). The resulting compound was confirmed by LC-MS and 1H NMR.

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Young Kuk; Kim, Kwang Hyun; Lee, Uhn Young; (77 pag.)KR2015/39485; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, Adding some certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0.

To 10 mL of Acetonitrile were added 3 mmol (1.05 g) of methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate (WO 2012/018635) 3.3 mmol (376 mg) of 2-mercapto-1-methylimidazole and 6.6 mmol (910 mg) of K2C03. The solution was stirred at room temperature overnight. When TLC showed no remaining methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate the reaction mixture was diluted with 10 mL of water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na2S04 and evaporated under reduced pressure. The crude product was then purified by recrystallization from ethanol to yield 1.04 g of yellow crystals (81 % yield). 1H NMR (200 MHz, DMSO-cf6) d 8.66 (d, J = 1.9 Hz, 1 H), d 8.34 (d, J = 1.8 Hz, 2H), d 7.28 (s, 1 H), d 6.87 (s, 1 H), d 3.91 (s, 3H), 3.51 (s, 3H), d 3.10 (s, 3H), d 2.92 (s, 3H). MS m/z: not found

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 60-56-0.

Reference:
Patent; UNIVERSITAeT WIEN; ERKER, Thomas; SCHREPPEL, Philipp; (235 pag.)WO2019/193159; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 670-96-2, name is 2-Phenyl-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 670-96-2, Safety of 2-Phenyl-1H-imidazole

General procedure: A mixture of Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand II (21.6 mg, 0.020 mmol), and F-PEG (0.25 g, 0.10 mmol) in MeOH (1 mL) was heated to dissolve all the reagents added completely and MeOH was removed under the reduced pressure. H2O (6 mL) was added to the residue and then 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol) and imidazole (2a, 13.6 mg, 0.20 mmol) were added. The whole reaction mixture was stirred under an O2 atmosphere at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL×3). The organic layer was washed with H2O (10 mL×3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (26.4 mg, 78%).

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

Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem