Author: Jessica.F

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2.

Add tetrakis (triphenylphosphine) palladium (0) (500 mg) to a degassed suspension of H-IMIDAZOLE (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4- (2- ISOPROPOXYPHENYL)-1H-IMIDAZOLE (5.01 g, 73%) which is used without further purification in the next step.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, Adding some certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8.

To 100 mg (0.36 mmol) of (S)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-6-methyl-3,6-dihydro- 2H-1,3,4-oxadiazin-2-one (Intermediate 75) and 73 mg of 4-trifluoromethyl imidazole (0.54 mmol) dissolved in 2 mL of DMF was added 235 mg of powdered Cs2C03 (0.72 mmol) and the mixture was heated at 80 Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); 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. 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., 84946-20-3

A mixture of 14 2-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole (2) (261mg, 1mmol) and 133 tert-butyl 3-aminopyrrolidine-1-carboxylate (370muL, 2mmol) in NMP (2mL) was heated at 180C under microwave for 60min. After cooling down to room temperature, the mixture was treated with a saturated 134 NaHCO3 solution and extracted with EtOAc. The combined organic phases was washed with water (2 times), dried over Na2SO4, and evaporated in vacuo. The crude residue was purified by silica gel flash column chromatography to afford the 135 title compound 18 (168mg, 54%). 1H NMR (300MHz, CDCl3) delta=7.53 (d, J=7.8Hz, 1H), 7.18-7.05 (m, 3H), 7.05-6.91 (m, 4H), 5.20 (s, 2H), 3.77-3.60 (m, 3H), 3.54 (ddd, J=9.7, 7.9, 6.2Hz, 1H), 3.26 (dd, J=9.4, 4.1Hz, 1H), 2.25 (br s, 2H), 2.18-2.06 (m, 1H), 1.79-1.65 (m, 1H)ppm. 13C NMR (75MHz, CDCl3) delta=162.11 (d, J=246.1Hz), 156.76, 142.16, 135.93, 132.52 (d, J=3.1Hz), 127.43 (d, J=8.0Hz), 121.98, 120.25, 116.76, 115.87 (d, J=21.6Hz), 108.28, 58.73, 51.21, 48.95, 47.08, 34.70ppm. HRMS m/z [M+H]+ calcd for C18H20FN4: 311.1666, found: 311.1662.

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; Tian, Junjun; Vandermosten, Leen; Peigneur, Steve; Moreels, Lien; Rozenski, Jef; Tytgat, Jan; Herdewijn, Piet; Van den Steen, Philippe E.; De Jonghe, Steven; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6332 – 6344;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4857-06-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4857-06-1 name is 2-Chloro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The N-methyl-1H-benzo[d]imidazol-2-amine, used as starting material, can be prepared as follows:2-Chloro-1H-benzo[d]imidazole (20 g, 131.08 mmol) was charged to high pressure autoclave PV10832 (Hastelloy 450 ml) with methylamine (260 mL, 131.08 mmol) and sealed on its trolley and the resulting solution heated to 160 C. in high pressure blast cell 60 for 16 hours. The pressure in the autoclave reached 11 bar. The solvent was removed under reduced pressure to afford a brown oil. EtOH was added and the solvent again removed to afford a brown foam. The foam was dissolved in a minimum of hot acetone. This was then allowed to cool. The resultant solid was filtered affording N-methyl-1H-benzo[d]imidazol-2-amine (9.91 g, 51%); 1H NMR (400 MHz, DMSO-d6) 2.83 (3H, s), 6.87-7.00 (2H, m), 7.05-7.25 (2H, m), 7.49 (1H, s).

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

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9, 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of imidazole-4,5-dicarboxylic acid (400 mg, 2.56 mmol) in 5 mL of toluene was added 1.12 mL of thionyl chloride (15.38 mmol) and 0.1 mL of DMF at rt. The reaction mixture was stirred at 90 C for 16 h. Then 5 mL of DCM was added to the suspension and the solvent was removed by evaporation. This process was repeated twice. The resulting acid chloride was dissolved in 10 mL of DCM and cooled to 0 C. Phenol (2.82 mmol) in 5 mL of DCM was added and the resulting solution was stirred at 0 C for 1 h. Then the solid product was collected by vacuum filtration, washed with 10 mL of DCM twice, and dried under vacuum to yield 0.632 g of crude product 17 (83.6 % over two steps) as a tan solid. 1H NMR (300Hz, DMSO) delta 9.12 (s, 2H), 7.52-7.56 (m, 4H), 7.34-7.40 (m, 6H); ESI-MS: 429 [M+1]+

The synthetic route of 1H-Imidazole-4,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Serrao, Erik; Xu, Zhong-Liang; Debnath, Bikash; Christ, Frauke; Debyser, Zeger; Long, Ya-Qiu; Neamati, Nouri; Bioorganic and Medicinal Chemistry; vol. 21; 19; (2013); p. 5963 – 5972;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Complexes 1-4 were prepared in a Schlenk tubecontaining 30 mL of CH2Cl2 (deaerated previously).Then, 0.24 mmol of the ligand and 32 muL of triethylaminewas added to the Schlenk. Afterwards, 0.11 mmol of theprecursor [RuCl2(dppb)(PPh3)] was added and the solutionwas stirred for 12 h under Ar atmosphere. The final yellowsolutions were concentrated to about 2 mL and diethyl etherwas added, to obtain yellow precipitates. The solids werefltered off, well rinsed with water (5 ¡Á 5 mL) and diethylether (3 ¡Á 5 mL) and dried in vacuo.

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:
Article; Batista, Alzir A.; Castellano, Eduardo E.; Castelli, Silvia; Cominetti, Marcia R.; Deflon, Victor M.; Desideri, Alessandro; da Silva, Monize M.; de Camargo, Mariana S.; de Grandis, Rone A.; Journal of the Brazilian Chemical Society; vol. 31; 3; (2020); p. 536 – 549;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. 1450-93-7

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. A solution of 799 mg of NaNO2 in 2 mL of water is added dropwise, and the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.65 g of 1,4-diallyl-1,2,3,4-tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and the dark solid is dried. (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diallyl-1,2,3,4-tetrahydroquinoxaline (2.3 g) is used in the next step without further purification.

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 1450-93-7.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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.

Intermediate 14: step b (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone A solution of EtMgBr (3.0 M in diethylether, 15.1 niL, 45.2 mmol) was added dropwise, to a solution of 5-bromo-l -methyl- 1H- imidazole (7.28 g, 45.2 mmol) in dry DCM (40 ml.) at 0 C and stirred for 10 minutes. The mixture was then stirred at room temperature for 30 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (8.45 g, 37.7 mmol, Intermediate 14: step a) dissolved in 22 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 18 hours. Water was added to the suspension followed by 6 M aqueous HC1 slowly to neutralize the mixture (pH = 6-7). More DCM was added and layers separated. The organic layer was dried over MgSC>4, filtered and concentrated. Et20 was added, the slurry sonicated, and precipitates were filtered and dried to provide the title compound.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

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

A common compound: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 41716-18-1

Production Example 9 N-(3-Bromo-4-fluorobenzyl)-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide A solution of methyl-1H-imidazole-4-carboxylic acid (1.17 g), N-(3-bromo-4-fluorobenzyl)cyclobutanamine (2.40 g) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) (3.09 g) in methanol (25 mL) was stirred at room temperature for 4 hr. After the reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate solution. After extraction with chloroform, the organic phase was dried over anhydrous magnesium sulfate. The desiccant was filtered off and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=98:2-92:8) to afford the title compound (469 mg). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.50-1.76 (m, 2H), 1.98-2.26 (m, 4H), 3.65-3.80 (m, 3H), 4.47-5.94 (m, 3H), 6.93-7.56 (m, 5H) (ESI pos.) m/z: 366([M+H]+), 368([M+3]+)

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, 41716-18-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Moriya, Minoru; Yasuhara, Akito; Sakagami, Kazunari; Ohta, Hiroshi; Abe, Kumi; Yamamoto, Shuji; Araki, Yuko; Urabe, Hiroki; Sun, Xiang-Min; US2013/184460; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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. 7098-07-9

Intermediate la 1 -Ethyl-5 -iodo- 1 H-imidazole In a 100 mL three-necked flask, TMEDA (2.86 g, 3.72 ml, 24.7 mmol, Eq: 2.37) was combined with pentane (10 ml) to give a colorless solution. N-BuLi 1.6M in hexane (15.6 ml, 25.0 mmol, Eq: 2.4), followed by 1 -ethyl- 1 H-imidazole (1 g, 10.4 mmol, Eq: 1.00) were added dropwise at -25¡ãC for 30 min. The reaction mixture was stirred at RT for 1 h (light yellow suspension). Afterwards, the suspension was cooled to -65¡ãC and THF anhydrous (30 ml) was added (-65¡ãC to -48¡ãC). A solution of iodine (3.83 g, 15.1 mmol, Eq: 1.45) in THF anhydrous (20 ml) was added dropwise to the reaction mixture (internal temperature remained below -55¡ãC) => brown suspension. Stirring was continued as the reaction was gradually warmed to 0¡ãC during 1.3 hours (brown milky solution). Eventually, the reaction was quenched by adding 4 mL of methanol. Work up: The reaction mixture was poured into 50 mL sat. Na2S03 and extracted with EtOAc (2 x 100 mL). The organic layers were combined, washed with brine, dried over Na2S04, and concentrated i. V. Purification : The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 100percent EtOAc in heptane) to provide in the more polar fractions 417 mg of the desired title compound as yellow oil. MS (ESI): 222.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7098-07-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans, P.; MAYWEG, Alexander, V.; MOHR, Peter; TAN, Xuefei; WO2013/120771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem