Category: imidazoles-derivatives

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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H9N3

The intermediate materials of Pt(ppy)ppyHCl and Pt(ppy)2C12 may be prepared using a previously reported procedure (Inorg. Chem. 2010, 49, 11297-11308, which is incorporated by reference herein in its entirety). Briefly, a mixture of 2-phenylpyridine and potassium tetrachloroplatinate in tert-butanol and water is heated to reflux to provide Pt(ppy)ppyHCl, which is then reacted with 5H-benzo[d] benzo[4,5]imidazo[1 ,2-a]imidazole in the presence of potassium carbonate in dichloromethane at reflux to provide Compound 301.

According to the analysis of related databases, 28890-99-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Chen, Hsiao-Fan; Silverstein, Daniel W.; Brooks, Jason; Feldman, Jerald; (143 pag.)US2018/331306; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, These common heterocyclic compound, 288-32-4, name is 1H-Imidazole, 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.

Anhydrous THF (25 mL) was cooled in an ice bath. After NaH (1.40 g, 35 mmol, 60%) was added to the THF in one portion, the mixture was stirred at rt for 30 min and cooled in an ice bath. Then a solution of 1H-imidazole (2.00 g, 30 mmol) in anhydrous THF (6 mL) was added dropwise. The reaction mixture was then warmed to rt and stirred at rt for 1.5 h. To the mixture was added 1-bromo-3-chloropropane (4.60 g, 30 mmol) dropwise, and stirred at rt overnight. To the resulting mixture was added MeOH (5 mL) in one portion. The resulting mixtue was filtered and the filtrate was concertrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=30:1) to give the title compound as pale yellow oil (3.10 g, 73%).

Statistics shows that 1H-Imidazole is playing an increasingly important role. we look forward to future research findings about 288-32-4.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Among them, “·” represents a boron hydrogen bond B-H. n-BuLi (1.6M) in n-hexane solution (1.00mL, 1.6mmol) was slowly added dropwise to the ortho-carboborane-o-C2B10H10 at -78 C(92.0 mg, 0.64 mmol) in tetrahydrofuran solution, stirring at this temperature for 30 minutes,After slowly increasing to room temperature, the reaction was continued for 1 hour and then bromobenzimidazole was added.(126.7 mg, 0.64 mmol), continued to react at room temperature for 6 hours. Then, the binuclear ruthenium compound [Cp*RhCl2] 2 (256.0 mg, 0.32 mmol) was added to the reaction system for further reaction for 3 hours.After completion of the reaction, the mixture was allowed to stand for filtration, and the solvent was evaporated to dryness, and the obtained crude product was subjected to column chromatography (petrole ether / THF / 6:1) to give a red target product (III).Complex Rh (265.6 mg, yield 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromobenzimidazole, its application will become more common.

Reference:
Patent; Shanghai Institute of Technology; Yao Zijian; Fan Xiaonan; Gao Yonghong; Deng Wei; (9 pag.)CN110117299; (2019); A;,
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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.

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:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 66121-69-5, name is 1-Methyl-1H-imidazole-4-carbonitrile, 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 66121-69-5, Product Details of 66121-69-5

43.4 ml 1 .4M methylmagnesiumbromide in toluene were added dropwise to a mixture of 5.0 g 1 -methyl-1 H-imidazole-carbonitrile in 70 ml diethylether at 0C. After 30 min , the mixture was warmed up to ambient temperature. After 1 h the reaction was quenched with 1 M aqueous HCI solution and neutralised with saturated sodium bicarbonate solution. The reaction mixture was extracted with dichloromethane. The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography (dichloromethane/methanol = 98/2) to give the intermediate 3.3. Yield: 4.8 g of 3.3 (75% content; 62% of theory); Analysis: [M+H]+ = 125

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; DOLLINGER, Horst; GNAMM, Christian; FIEGEN, Dennis; HOFFMANN, Matthias; LAMB, David, James; KLICIC, Jasna; SCHNAPP, Andreas; WO2013/156608; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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. HPLC of Formula: C11H12BrFN2

3.5 g of 6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole was dissolved in 20 ml of DMF.And add 5.1g of (BPin) 2, 0.62g of PCy3, 3.8g of KOAc and 0.3g of Pd(OAc)2, stir and heat to 100 C for 24h, stop heating and cool down to 6At 0 C, 50 ml of ethyl acetate was added, and the mixture was filtered.Add n-hexane to the oil obtained by concentration, stir and crystallize for 1 h at room temperature.Filtration gave 2.1 g of 4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-boronic acid pinacol ester as a pale yellow solid.

The synthetic route of 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24155-42-8, These common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, 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.

EXAMPLE 2 2,6-Dichloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:1) 8.7 g of 4-bromomethyl-2,6-dichloroquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g of sodium hydroxide (0.75 mol) dissolved in 30 ml water, 0.5 g of benzyltrimethylammonium chloride and 100 ml of tetrahydrofuran are reacted as described in Example 1. Work up of the mixture results in an oil, which after treatment in boiling ether, is dissolved in 250 ml of ethyl acetate.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methyl-1H-imidazole-4-carbaldehyde

To a solution of 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine (0.02 g, 0.051 mmol) in dichloroethane (0.5 mL) in a two dram vial was added 4-methyl-1H-imidazole-5-carbaldehyde (6 mg, 0.051 mmol), followed by a drop of acetic acid. The reaction mixture was shaken for 20 minutes at room temperature and then NaBH(OAc)3 was added (12 mg, 0.056 mmol). The reaction was stirred at room temperature overnight. The solvents were removed and the residue was purified by preparative HPLC (phenominex C18 column, 21×100 mm, 5 mu) using MeOH/H2O (with 0.1% TFA) to give 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-N-((4-methyl-1H-imidazol-5-yl)methyl)-2-phenylethanamine as a white solid (23.4 mg, 76% yield). LCMS: 3.6 min [M+1] 489.2 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) delta ppm 2.27 (s, 3H), 3.45-3.52 (m, 1H), 3.88-3.99 (m, 2H), 4.01-4.07 (m, 1H), 6.64 (d, J=7.09 Hz, 2H), 7.02 (d, J=8.56 Hz, 1H), 7.10 (t, J=7.46 Hz, 2H), 7.18 (t, J=7.46 Hz, 1H), 7.49 (d, J=7.58 Hz, 1H), 7.61 (d, J=9.54 Hz, 1H), 7.69 (s, 1H), 7.76 (dd, J=8.56, 2.45 Hz, 1H), 8.28 (s, 1H), 8.60 (d, J=1.96 Hz, 1H).

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 68282-53-1.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/161685; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

A mixture of 2-(l-methyl-5-nitro-lH-imidazol-2-yl)-ethanol (1.25 mmol) and 2,4-di- chloro-l-fluorobenzene (1.45 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column:XBridge preparative C18 OBD column 19×150 mm, 5 urn; mobile phase A: water (10 mmol/L NH4HC03), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product- containing fractions were collected and then lyophilized to give 2-(2,4-dichloro-phenoxymethyl)- l-methyl-5-nitro-lH-imidazole. LC-MS: (ES, m/z) 302.00 (M+H)+; analysis: C, 43.78; H, 3.08; CI, 23.52; N, 13.81; O, 15.99.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H8N2O

The intermediate 1H-benzimidazole-2-methanol (1 g, 1 eq) and potassium permanganate (2.6 g. 1.5 eq) were added to dilute sodium hydroxide solution and heated at 100 ° C under reflux.After the reaction was completed, it was cooled to room temperature, the pH was adjusted to be acidic, and a brown solid was precipitated.Yield: 86percent.

The synthetic route of 4856-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Yu Jing; (20 pag.)CN110105286; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem