Author: Jessica.F

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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

General procedure: To a solution of 5-bromo-lH-benzo[d]imidazol-2(3H)-one80 (50 mg) in dioxane (1 ml) were added pyridin-3-ylboronic acid 81 (43.3 mg), [l,l-bis(diphenyl- phosphino)ferrocene]dichloropalladium(II) (17.2 mg) and 2 M aq. sodium carbonate solution (235 mu). The reaction mixture was heated at 100 C for 18 hours. The reaction mixture was then cooled to room temperature, diluted with water (50 ml), and extracted twice with ethyl acetate (2 x 30ml). The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel; 12 g; eluent: dichloromethane/methanol = 100/0 to 95/05 in 10 minutes) to afford 5-(pyridin-3-yl)-lH- benzo[d]imidazol-2(3H)-one (12 mg, 23%) as a red solid. MS (ISP): 212.1 ([M+H]+).

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15965-31-8,Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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.

Synthesis of 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole To a stirred solution of 1-chloro-2-methoxy-4-nitrobenzene (4 g, 39.21 mmol) in DMSO (40 mL) under an argon atmosphere were added 4-chloro-1H-imidazole (7.3 g, 39.21 mmol) and potassium hydroxide (2.2 g, 39.21 mmol) at RT. The reaction mixture was stirred at 80 C. for 20 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with water (600 mL), filtered, washed with water (2*50 mL) and dried in vacuo to afford 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (3.8 g, 70%) as a brown solid which was used without further purification. 1H-NMR (CDCl3, 400 MHz): delta 7.98-7.94 (m, 2H), 7.75 (s, 1H), 7.44 (d, 1H), 7.19 (s, 1H), 4.01 (s, 3H); LC-MS: 254.1 (M+1); (column; X-Bridge C-18 (50*3.0 mm, 3.5 lam); RT 3.05 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 30% EtOAc:hexanes (Rf: 0.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-1H-imidazole, its application will become more common.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 96797-15-8, name is 4-Iodo-1-trityl-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 96797-15-8, Recommanded Product: 4-Iodo-1-trityl-1H-imidazole

4-iodo-1-trityl-1H-imidazole (38.7 g, 88.8 mmol), (2-formylphenyl)boronic acid (20.0 g, 133 mmol)And K3PO4 (56.4 g, 266 mmol) was dissolved in 1,4-dioxane (300 mL) and water (60 mL).Nitrogen gas was bubbled through the reaction solution for 5 min, then Pd(PPh3)4 (5.12 g, 4.44 mmol) was added, and the reaction mixture was bubbled with nitrogen for 5 min.The reaction was heated at 90 C for 16 h under nitrogen.After the reaction was completed, the temperature was lowered, and the celite was filtered, and the filtrate was diluted with water (100 mL) and EA (300 mL), and the mixture was allowed to stand for separation. The aqueous phase was extracted with EA (300 mL×2; combined organic phase, water (100 mL) and saturated brine (100 mL × 3) washing.The organic phase was concentrated under reduced pressure to give a residue.Purified with PE/EA=3/1 column,Obtained a light brown viscous oil 2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (15.0 g, 40.8%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
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 6160-65-2 as follows. name: 1,1′-Thiocarbonyldiimidazole

To a stirred solution of 1-Z-piperazine (8.5 g, 38.5 mmol) in dry THE (100 mL), 1,1- thiocarbonyldimidazole (12.37 g, 69.4 mmol) was added and the mixture was stirred at 60C for 5 h. It was concentrated under vacuum and NH3 in EtCH (2 N, 300 mL) was added at 0C. The resulting mixture was stirred at 55C for 8 h in an autoclave. It was diluted withwater (100 mL) and extracted with DCM (2 x 100 mL). The DCM layer was washed with water (100 mL), dried over in anhydrous Na2SO4 and concentrated. The resulting crude product was purified by flash chromatography to afford the title product. Yield: 87% (7 g, white solid). 1H NMR (400 MHz, DMSO-d6): 6 7.51 (5, 2H), 7.38-7.31 (m, 5H), 5.1 (5, 2H), 3.78 (m, 4H), 3.43-3.33 (m, 4H). LCMS: (Method A) 280.2 (M+H), Rt. 2.33 mm, 95.4% (Max).

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 621-72-7, name is 2-Benzyl-1H-benzo[d]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 621-72-7, Recommanded Product: 621-72-7

To the reaction vessel was added 8.2 g of dibazole,63 g of 10 wt% hydrochloric acid solution and 1.2 g of activated carbon,Air was introduced into the reaction vessel while stirring, and the temperature was raised to 95 C.The reaction was stirred for 10 hours while the reaction was completed, and the air was stopped.Drop to 15 C, filter, and evaporate the filtrate under reduced pressure to give 8.5 g of crude material;The crude product was mixed with 70 g of anhydrous methanol and stirred and dissolved at 55 C.The mixture was filtered while hot, and the filtrate was stirred at 0 C for 3 hours, and filtered.Drying, 7.8 g of diazol oxidized impurity reference substance was obtained, and the yield was 89.3%.The purity was determined by HPLC to be 99.95%.

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-Benzyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan Xian Lu Pharmaceutical Technology Co., Ltd.; Huang Li; Ning Fan; Wu Bo; Wang Ge; Xie Shuwei; Chen Weijiang; (6 pag.)CN108863946; (2018); 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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-(4-Nitrophenyl)-1H-imidazole

General procedure: To a stirring solution of 4-CNPy (104 mg, 1.0 mmol, 2 equiv) in ethanol (25 ml), Ru(NO)Cl3·2H2O (136 mg, 0.5 mmol, 1 equiv) was added and contents of the flask heated under reflux for 12 h. After cooling to room temperature a red solid separated which was isolated by filtration, washed with ethanol, diethylether and dried under vacuo. Crystals suitable for X-ray diffraction analyses were obtained by slow diffusion of hexane into dichloromethane solution of the complex. Yield: 138 mg (62%),

The synthetic route of 2301-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Amit; Pandey, Rampal; Gupta, Rakesh Kumar; Ghosh, Kaushik; Pandey, Daya Shankar; Polyhedron; vol. 52; (2013); p. 837 – 843;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

General procedure: The aryl carboxylic acid (1.1 eq.) and TBTU (1.2) were suspended in anhydrous THF (11 mL/mmol eq.) at r.t. under N2 atmosphere. DiPEA (2.4 eq.) was then added dropwise to the reaction mixture,followed by the different (thieno[2,3-d]pyrimidin-4-yl)-hydrazine (8a-d or f-i) (1 eq.) dissolved in anhydrous THF (11 mL/mmol eq.). The mixture was stirred at r.t. for 4 h, then concentrated under vacuum. The residue was dissolved in EtOAc (30 mL/mmol eq.), washed with water (30 mL/mmol eq.), saturated NaHCO3 solution (30 mL/mmol eq.), and finally with brine (30 mL/mmol eq.). The organic phase was concentrated under vacuum after drying over MgSO4. The crude residue was purified by recrystallisation or flash column chromatography.

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; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 31 – 47;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-84-0, A common heterocyclic compound, 1072-84-0, name is 1H-Imidazole-4-carboxylic acid, molecular formula is C4H4N2O2, 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.

To a mixture of 1H-imidazole-4-carboxylic acid (5.00 g, 44.6 mmol, CAS1072-84-0) in MeOH (50 mL) was added SOCl2 (10.6 g, 89.2 mmol, 6.47 mL). The reaction mixture was stirred at 70 C. for 16 hours. On completion, the reaction mixture was concentrated in vacuo to give the title compound (5.60 g, 99% yield) as white solid. The residue was used to the next step directly without further purification. 1H NMR (400 MHz, DMSO-d6) delta 9.29-9.25 (m, 1H), 8.37 (s, 1H), 3.87 (s, 3H).

The synthetic route of 1072-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

300 mg of 3 (1 eq., 0.55 mmol), 86 mg of 1 (1 eq., 0.55 mmol),326 mg of Cu(OAc)2·H2O, 18 mg of potassium iodide (0.2 eq.,0.11 mmol) and 6 mg of Pd(OAc)2 were dissolved in 3 mL of dimethylsulfoxide and 12 mL acetonitrile. The reaction vessel was set under anatmospheric pressure of carbon monoxide (CAUTION: highly toxic) andshortly warmed with a hot water bath (40 C). After 1 h the reactionmixture was taken up in EtOAc and washed with sat. NaHCO3 andwater. The combined aqueous solutions were washed with EtOAc andthe combined organic solutions were washed with brine, dried overMgSO4 and the solvent was removed under reduced pressure. The crudeproduct was dried in vacuo overnight. Purification was performed usingcolumn chromatography (EtOAc/petrol ether 9:1). Yield: 160 mg(40%). 1H NMR (500 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.65 (s, 1H), 8.41(s, 1H), 8.23 (s, 2H), 7.84 (s, 1H), 7.54 (dd, J = 8.9, 5.0 Hz, 1H), 7.45(t, J = 8.7 Hz, 1H), 7.38 (s, 1H), 7.28 (s, 1H), 6.15 (d, J = 6.6 Hz, 1H),5.30 – 5.19 (m, 2H), 4.52 (t, J = 10.9 Hz, 1H), 3.96 (s, 3H), 3.10 (dd,J = 23.1, 11.6 Hz, 2H), 2.23 (d, J = 11.4 Hz, 2H), 2.15 – 2.06 (m, 2H),1.73 (d, J = 6.6 Hz, 3H), 1.43 (s, 9H) ppm. ESI-MS (M + Na): calc:755.19 found: 755.39.

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

Reference:
Article; Berger, Walter; Bielec, Bjoern; Heffeter, Petra; Keppler, Bernhard K.; Kowol, Christian R.; Schueffl, Hemma; Terenzi, Alessio; Bioorganic Chemistry; vol. 99; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 87941-55-7, These common heterocyclic compound, 87941-55-7, name is 4-Bromo-1-trityl-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.

To a suspension of 3.00 g (7.71 mmol) of 4-bromo-1-trityl-1H-imidazoie in 30 ml of dioxane1.58 g (9.23 mmol) of 4-methoxymethyi boronic acid, 3.47 g (10.5 mmol) of cesiumcarbonate and 0.121 g (0.131 mmol) of tris-(dibenzylideneaceton)dipalladium are added, followed by 0.315 ml (0.308 ml) of a solution of 5 g of tri-t-buylphosphine in 25 ml of dioxane. The mixture is heated at 80C and stirred for 6.5 hours. After cooling to room temperature the suspension is diluted with dichloromethane and filtered, the filter cake washed with ethyl acetate and the filtrate concentrated to dryness. The residue is purified by flash chromatography on silica (40 – 63 urn particle size) with hexane / ethyl acetate 7:3, yielding 2.805 g of 4-(4-methoxymethyl-phenyl)-1-trityl-1H-imidazole, Rt = 4.659 min by HPLC on a nucleosil C18HD column with acetonitril + 0.05% TFA / water + 0.05% TFA, 20/80 to 100/0 over 6 min, 1.0 ml/min solvent flow. MS (API-ES, pos. scan): e/m = 431 (M+1).

Statistics shows that 4-Bromo-1-trityl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 87941-55-7.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/10591; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem