Category: 25676-75-9

Ren, Yun-lai et al. published their research in Fenzi Cuihua in 2014 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Product Details of 25676-75-9

Nitrogen dioxide-catalyzed oxidative bromination of benzenes and naphthalines with electron-donating substituents at room temperature was written by Ren, Yun-lai;Wang, Qian;Tian, Xin-zhe;Wang, Bin-yu;Wang, Pei. And the article was included in Fenzi Cuihua in 2014.Product Details of 25676-75-9 This article mentions the following:

Oxidative bromination of benzenes and naphthalines with electron-donating substituents was investigated by using 8.2% nitrogen dioxide as the catalyst, the residual oxygen in the reaction tube as the oxidant, and mol. bromine as the brominating reagent at room temperature The used heavy metal waste-free catalyst can be easily removed from the products and scarcely stains the final products. But a small amount of byproduct from the nitration of the benzene ring was observed, which led to the consumption of nitrogen dioxide. The reaction is highly atom economic, and a majority of bromine atoms in bromine source were transferred to the bromination products. The bromination was controllable: mono- and di-bromination products were controllably obtained by changing the loading amount of the brominating reagent. Preliminary mechanistic investigation suggests that the bromination firstly undergoes the reaction between mol. bromine and aromatic ring to give aryl bromide and HBr, which is followed by oxygenation of the resulting bromine hydride to form the reactive bromine under the catalysis of the catalytic species. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Product Details of 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Product Details of 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Conn, Edward L. et al. published their research in Organic & Biomolecular Chemistry in 2022 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3鈥揅6) is higher than in water and generally decreases with a Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Product Details of 25676-75-9

Identification of parallel medicinal chemistry protocols to expand branched amine design space was written by Conn, Edward L.;Perry, Matthew A.;Shi, Kecheng;Wang, Guotao;Hoy, Susan;Sach, Neal W.;Qi, Wenying;Qu, Liqiang;Gao, Yu;Xu, Yan;Schmitt, Daniel C.. And the article was included in Organic & Biomolecular Chemistry in 2022.Product Details of 25676-75-9 This article mentions the following:

Methods for the synthesis of 伪-branched heteroaryl amines RCH(R1)NH(R2) (R = tert-Bu, Ph, 1-methyl-1H-imidazol-4-yl, pyridin-2-yl, etc. R1 = 1-methyl-1H-pyrazol-5-yl, pyridin-3-yl, 1-propyl-1H-pyrazol-4-yl, 4-bromo-2-hydroxyphenyl, etc.; R2 = pyridin-2-yl, Ph, 4-phenylpyridin-2-yl, pyrazin-2-yl, etc.) via aldimine addition have been evaluated for compatibility with parallel synthesis. In situ activation of aliphatic carboxylic acids RC(O)OH as redox-active esters enables Zn-mediated decarboxylative radical imine R1CH=NR2 addition to access aliphatic-branched heterobenzylic amines. In situ activation of (hetero)aryl bromides RBr via Li-halogen exchange enables heteroaryl-lithium addition to imines to access (hetero)benzhydryl amines. Condensation of heteroaryl amines RNH2 with heteroaryl aldehydes R1CHO provides aldimines which may be intercepted with aryl Grignard reagents to provide modular access to (hetero)benzhydryl amines. These protocols minimize synthetic step count and maximize accessible design space, enhancing access to 伪-branched heteroaryl amines for medicinal chem. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Product Details of 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3鈥揅6) is higher than in water and generally decreases with a Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Product Details of 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Wang, Mo et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2014 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C4H5BrN2

Cu-catalyzed amidation of halogenated imidazoles was written by Wang, Mo;Zhang, Zhenfeng;Xie, Fang;Zhang, Wanbin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.Synthetic Route of C4H5BrN2 This article mentions the following:

An efficient methodol. involving the Cu-catalyzed amidation of halogenated imidazoles has been successfully developed. The amidated product of 5-bromo-1-alkylimidazole was further applied to the synthesis of a new chiral imidazole nucleophilic catalyst for the kinetic resolution of secondary alcs. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Synthetic Route of C4H5BrN2).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C4H5BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

El Borai, M. et al. published their research in Polish Journal of Chemistry in 1981 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Recommanded Product: 4-Bromo-1-methylimidazole

Synthesis of halogen derivatives of N-methylimidazole was written by El Borai, M.;Moustafa, A. H.;Anwar, M.;Abdel Hay, F. I.. And the article was included in Polish Journal of Chemistry in 1981.Recommanded Product: 4-Bromo-1-methylimidazole This article mentions the following:

1-Methylimidazole (I) was converted to 2-halo-, 2,5-dihalo-, 5-halo-, 2,4-dihalo-, 4,5-dihalo-, 4-halo-, and 2,4,5-trihalo-1-methylimidazoles. I was treated with BuLi and Br2 to give 2-bromo-1-methylimidazole. The reaction of I with N-bromosuccinimide gave 5-bromo-1-methylimidazole. I reacted with iodine and HIO3 to give 4,5-diiodo-1-methylimidazole. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Recommanded Product: 4-Bromo-1-methylimidazole).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Recommanded Product: 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ohba, Masashi et al. published their research in Heterocycles in 1992 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Quality Control of 4-Bromo-1-methylimidazole

Synthesis of 5-arylthio-3-methyl-L-histidine, a model for the starfish alkaloid imbricatine was written by Ohba, Masashi;Mukaihira, Takafumi;Fujii, Tozo. And the article was included in Heterocycles in 1992.Quality Control of 4-Bromo-1-methylimidazole This article mentions the following:

Syntheses of 3-methyl-5-phenylthio-L-histidine (I, R = Ph) and 3-methyl-5-(1-naphthyl)thio-L-histidine ( R = 1-naphthyl), selected as models for the asteroid alkaloid imbricatine (II), have now become feasible through a 10-step route starting from 4(5)-bromoimidazole. The key steps involve replacement of the 4-bromo group by an arylthio group in the aldehyde III and construction of the L-alanine moiety in the chlorides IV by the “bis-lactim ether” method. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Quality Control of 4-Bromo-1-methylimidazole).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Quality Control of 4-Bromo-1-methylimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Liu, Dandan et al. published their research in Chinese Chemical Letters in 2022 | CAS: 25676-75-9

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Recommanded Product: 25676-75-9

Design, synthesis and SAR study of 2-aminopyridine derivatives as potent and selective JAK2 inhibitors was written by Liu, Dandan;Ge, Huan;Xu, Fangling;Xu, Yufang;Liu, Wenjun;Li, Honglin;Zhu, Lili;Diao, Yanyan;Zhao, Zhenjiang. And the article was included in Chinese Chemical Letters in 2022.Recommanded Product: 25676-75-9 This article mentions the following:

The abnormal activation of JAK2 kinase is closely related to the occurrence and progression of myeloproliferative neoplasms (MPNs). At present, there is still an obvious unmet medical need for selective JAK2 inhibitors in clinic. In this paper, a class of 2-aminopyridine derivatives as potent and selective JAK2 inhibitors was obtained by combining drug design, synthesis and structure-activity relationship studies based on the previously identified lead Crizotinib. Among them, I exhibited high inhibitory activity against JAK2 with an IC50 of 9 9 nmol/L, moreover, it showed 276- and 184-fold selectivity over JAK1 and JAK3, resp. Besides, I had a significant antiproliferative activity against HEL cells, and also inhibited the phosphorylation of JAK2 and its down-stream signaling pathway. These results indicated that 2-aminopyridine compound I had the potential to be developed as a selective JAK2 inhibitor for further study. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Recommanded Product: 25676-75-9).

4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Recommanded Product: 25676-75-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

9/6/21 News Sources of common compounds: 25676-75-9

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Synthetic Route of 25676-75-9, 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 25676-75-9 as follows.

Step 1: A solution of 4-bromo-1-methyl-1H-imidazole (1.0 g, 6.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (1.0 g, 6.5 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.6 g, 0.52 mmol) and aqueous Na2CO3 (2 M, 4 mL, 8.0 mmol) in a mixture of DME/EtOH/H2O (7:3:2, 10 mL) was evacuated and then refilled with nitrogen (three cycles). Resulting reaction mixture was then irradiated in the microwave at 150 C. for 50 min., dried (MgSO4), filtered and concentrated under reduced pressure to give a black residue, which was purified by column chromatography eluting with MeOH/DCM to provide 4-(4-fluoro-3-methylphenyl)-1-methyl-1H-imidazole (0.6 g, 51%). MS m/e: 191 (M+H)+.

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; Bristol-Myers Squibb Company; Kinsella, Todd; Gelman, Marina; Hong, Hui; Darwish, Ihab S.; Singh, Rajinder; Yu, Jiaxin; Borzilleri, Robert M.; Velaparthi, Upender; Liu, Peiying; Darne, Chetan; Rahaman, Hasibur; Warrier, Jayakumar Sankara; (311 pag.)US2016/257690; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Continuously updated synthesis method about C4H5BrN2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methylimidazole, its application will become more common.

Application of 25676-75-9,Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

Example 39 N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-1 -(1 -methyl-1 H- imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (E39) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a stirred mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4- imidazolidinecarboxamide (100 mg, 0.33 mmol) (prepared as described in Example 28), 4-bromo-1 -methyl-1 H-imidazole (63.8 mg, 0.396 mmol) in 1 ,4-dioxane (6 ml) was added potassium phosphate (350 mg, 1.65 mmol), copper (I) iodide (62.8 mg, 0.33 mmol) and trans-N,N-dimethylcyclohexane-1 ,2-diamine (0.052 ml, 0.33 mmol) and the mixture was heated at reflux under argon for 1 h. The mixture was cooled to room temperature and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by silca gel chromatography eluting with 0-20% methanol in dichloromethane, followed by mass- directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1- (1-methyl-1 H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (15 mg, 12%). LC/MS [M+H]+ = 384 , retention time = 1.71 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methylimidazole, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4-Bromo-1-methylimidazole

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-methylimidazole, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 25676-75-9, name is 4-Bromo-1-methylimidazole, 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 25676-75-9, HPLC of Formula: C4H5BrN2

To a solution of (4S)-6,8-dichloro-2-methyl-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,3,4-tetrahydroisoquinoline (50 mg) obtained in Reference Example 3-2 in dioxane (1.0 mL) and water (0.25 mL), 4-bromo-1-methyl-1H-imidazole (14 mg), tri(2-furyl)phosphine (17 mg), cesium carbonate (78 mg), and tris(dibenzylideneacetone)dipalladium(0) (11 mg) were added in a nitrogen gas atmosphere, and the mixture was stirred at 90C for 1 day.The reaction solution was allowed to cool, and then, water was added thereto, followed by extraction with ethyl acetate.The organic layer was dried over anhydrous magnesium sulfate and filtered, and then, the filtrate was concentratedunder reduced pressure. The obtained residue was purified by preparative LC-MS (LC (Agilent 1260), ESIMS (6130Quadrupole, ESI), column (YMC-Actus Triart 5 mm C18 50 x 30 mm), mobile phase (0.1% formic acid in H2O:0.1%formic acid in CH3CN = 95:5 ? 50:50 ? 5:95), 50 mL/min.) to obtain the title compound (3.6 mg, yield: 6.7%) as acolorless oil substance. 1H NMR (300 MHz, CD3OD) delta ppm 2.60 (s, 3H), 2.80 (dd, J=11.8, 9.8Hz, 1H), 3.17-3.26 (m, 1H), 3.62-3.71 (m, 1H),3.76 (s, 3H), 4.01-4.12 (m, 1H), 4.37 (dd, J=9.8, 5.8Hz, 1H), 6.79-6.83 (m, 1H), 7.07 (d, J=7.6Hz, 1H), 7.31-7.38 (m,2H), 7.46 (s, 1H), 7.54-7.69 (m, 3H). MS (+): 372 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-methylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; KURODA, Shoichi; KAWABE, Kenichi; USHIKI, Yasunobu; OHTA, Hiroshi; UNEUCHI, Fumito; SHIBATA, Tsuyoshi; TABUSE, Hideaki; MUNETOMO, Eiji; CHONAN, Sumi; (140 pag.)EP3173408; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Share a compound : 25676-75-9

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 25676-75-9, A common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, its 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.

Intrmdiate Example 11.5-(I-Methyl-1H-imidazol-4-yl)-1H-benzo[d]imidazolea) 4-(1-Methyl-1H-imidazol-4-yl)-2-nitroanilineA solution, of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(1.45 g, 5.55 mmol, 1.1 eq) in 1 ,2-dimethoxyethane (15 ml) was degassed by N2bubbling for 5 mi 4-Bromo-1-methyi-1H-imidazole (0.81 g, 5 mmol, 1 eq) was added and the mixture was degassed for another 5 mm. Pd(dppf)Cl2 (0.4 g, 0.5 mmol, 0.1 eq) and aqueous sodiumcarbonate (1.59 g, 15 mmol, 3 eq) were added, sequentially using the procedure of Intermediate Example 1 and then heated at 100 C for 4 h. The reactionmixture was then quenched and extracted as in Intermediate Example 1. The solvent was distilled off to afford the crude residue which was purified by columnchromatography (60-120 silica gel, 50 % ethyl acetate in hexane) to afford the title product in 60 % yield (0.6 g). LC-MS (ESI): Calculated mass: 218.08; Observed mass:219.2 [M+HJ (rt: 0.09 mm).

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; RAJAGOPALAN, Srinivasan; APPUKUTTAN, Prasad; NARASINGAPURAM ARUMUGAM, Karthikeyan; UJJINAMATADA, Ravi Kotrabasaiah; GEORGE, Shyla; LINNANEN, Tero; WO2014/162039; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem