Month: March 2021

Reference of 118469-15-1, A common heterocyclic compound, 118469-15-1, name is 5-Fluoro-2-methyl-1H-benzo[d]imidazole, molecular formula is C8H7FN2, 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.

(0621) A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (499 mg, 2.33 mmol) and 5-fluoro-2- methyl-1H-benzo[d]imidazole (350 mg, 2.33 mmol) in DMF (15 mL) was stirred at 16 C for 16 h. The mixture was washed with water (50 mL) and extracted with EtOAc (3 x 30 mL). The collected organic layers were washed with brine (30 mL) and dried over anhydrous Na2SO4. The mixure was filtered and the filtrate was concentrated to get the crude product. The crude product was purified by reverse-phase Prep-HPLC (preparative HPLC on a GILSON 281 instrument fitted with Phenomenex Synergi C18 250×21.2mmx4um using water and acetonitrile as the eluents. Mobile phase A: water, mobile phase B: acetonitrile (containing: 0.1%TFA-ACN). Gradient: 35-65%, 0-10 min; 100% B, 10.5-12.5min; 5% B, 13-15min) to give 3-fluoro-4-((5- fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile as an oil. ESI-MS m/z [M + H]+ : 284.0.

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:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; WANG, Deping; FRALEY, Mark, E.; JONES, Kristen, G.; (273 pag.)WO2017/222951; (2017); 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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6F2N2

To a stirred solution of 3-(4,6-dichloro-1,3,5-triazine-2,4-diyl)(8-oxa-3-azabicyclo[3.2.1]octane) (2.61 g, 10 mmol) in acetone/ice, morpholine (900 mg, 12 mmol) and triethylamine (5 ml) was added. The reaction mixture was stirred at room temperature for 3 hours. Separated white solid was filtered and washed with water. The crude product obtained was pure enough and taken to next step without purification. Treatment of the mixture (270 mg. 0.87 mmol) with 2-(difluoromethyl)-1H-benzo[d]imidazole (146 mg, 0.87 mmol) and K2CO3 (967 mg, 7 mmol) in DMF (2.5 mL) for 18 hours gave 2-(difluoromethyl)-1-[4-morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]-1H-benzimidazole after purification by HPLC. (M+H) 445.

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; VENKATESAN, Aranapakam Mudumbai; CHEN, Zecheng; DEHNHARDT, Christoph Martin; DOS SANTOS, Osvaldo; DELOS SANTOS, Efren Guillermo; ZASK, Arie; VERHEIJEN, Jeroen Cunera; KAPLAN, Joshua Aaron; RICHARD, David James; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; GOPALSAMY, Ariamala; CURRAN, Kevin Joseph; SHI, Mengxiao; (113 pag.)US2017/119778; (2017); 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., name: 1H-Imidazole

General procedure: A mixture of aryl imidazoles (0.5 mmol), arylboronic acid (1 mmol), K2CO3 (1 mmol), C-1 complex (5 mol %, 9.79 mg) in iso-propanol (1.5 mL) was stirred in a 50 mL oven dried round bottomed flask. After the completion of the reaction (monitored by TLC), the mixture was diluted with 20 mL water. The organic part was extracted with diethyl ether (3 20 mL) followed by drying over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain the crude product. The residue was then purified with column chromatography using methanol/ethyl acetate (1:9) as eluent to afford the desired product. The purity of the compound was confirmed by 1H NMR, 13CNMR, MS, and melting point data. N-Phenyl imidazole (6a): 1H NMR (400 MHz, CDCl3, d ppm) 8.02 (s, 1H), 7.51-7.47 (m, 2H), 7.41-7.37 (m, 3H), 7.26 (s, 1H), 7.21 (s, 1H). 13C NMR (100 MHz, CDCl3, d ppm): 138.1, 135.9, 130.5, 130.1, 127.6, 121.8, 118.5.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gogoi, Ankur; Sarmah, Gayatri; Dewan, Anindita; Bora, Utpal; Tetrahedron Letters; vol. 55; 1; (2014); p. 31 – 35;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, 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 288-32-4 as follows.

General procedure: Under an O2 atmosphere, a mixture of 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol), imidazole (2a, 13.6 mg, 0.20 mmol), Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand I (3.7 mg, 0.020 mmol), and Triton X-100 (38.8 mg, 0.060 mmol) in H2O (4 mL) was stirred at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL¡Á3). The organic layer was washed with H2O (10 mL¡Á3) 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) (23.0 mg, 66%).

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:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
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. 5465-29-2, name is 2-Propylbenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Propylbenzimidazole

2-Propyl-benzimidazole (0.30 g, 1.87 mmol) was dissolved in acetonitrile (7 mL), potassium hydroxide (0.17 g, 3.03 mmol) was added, and the mixture was refluxed for 30 min. 2-(Bromomethyl)naphthalene (0.42 g, 1.90 mmol) was added and the mixture was refluxed overnight.

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; Shelton, Kerri L.; DeBord, Michael A.; Wagers, Patrick O.; Southerland, Marie R.; Williams, Travis M.; Robishaw, Nikki K.; Shriver, Leah P.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J.; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 421 – 439;,
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. 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Safety of 2-(2-Bromophenyl)-1H-benzo[d]imidazole

General procedure: First, 100 mmol of 2-(2-bromophenyl)imidazole derivatives introduced into 300 ml of triethylamine and 200 ml of DMF. And stirring continuously added to 200 ml alkyne, 5 mmol triphenylphosphine and 5 mmol of copper iodide (I) and 2 mmol palladium(II) acetate. The reaction mixture was then stirred for 20 hours at 80 . After cooling, the reaction mixture was diluted with 400 ml of methylene chloride, to separate a solid, by filtration through a bed of salt C and the filtrate was evaporated to dryness. The residue was dissolved in 300 ml of methylene chloride, 100 ml of concentrated aqueous ammonia with individual cleaning solution three times, and then washed three times with 100 ml of water, and dried over magnesium sulfate. With spherical fractionating tube distillation or sublimation, resulting in the manipulation of the vacuum pump oil / solids release low-boiling components and trace metals.

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:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; HEIL, HOLGER; JOOSTEN, DOMINIK; PFLUMM, CHRISTOF; GERHARD, ANJA; BREUNING, ESTHER; (214 pag.)TWI520958; (2016); B;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 1H-imidazole-5-carboxylate

c) 3-{[(2-Bromo-benzyl)-methyl-carbamoyl]-methyl}-3H-imidazole-4-carboxylic acid methyl ester; To a solution of N-(2-bromo-benzyl)-2-hydroxy-N-methyl-acetamide (1.02 g, 3.95 mmol) in THF (40 mL) at 0 0C is added triphenylphosphine (1.15 g, 4.36 mmol), methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.50 g, 3.96 mmol) and diisopropyl azodicarboxylate ( 0.85 mL, 4.36 mmol). The reaction is permitted to warm to room temperature and allowed to stir 18 hours. The reaction is then adsorbed directly onto silica gel and submitted to silica gel flash chromatography (diethylamine-methanol- dichloromethane, 1 :3:96) to provide 3-{[(2-bomo-benzyl)-methyl-carbamoyl]-methyl}-3H- imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 366.2, 368.2 (M+H)+.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 28890-99-5, 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. 28890-99-5 name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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.

a) 31.7 g (96.1 mmol) diiodobenzene, 14.9 g (72.1 mmol) 6H-benzimidazolo[1,2- a]benzimidazole, 23.5 g (72.1 mmol) cesium carbonate, 1.83 g (9.61 mmol) cupper (I) iodide, 2.21 g (19.3 mmol) L-proline in 400 ml DMSO was stirred under nitrogen at 100 C for3 h. The reaction mixture was poured in 600 ml water and the product was filtered off. The product is washed with water and ethanol. 100 ml diethyl ether is added and the mixture is stirred for 3 h. Product is filtered off and is washed with ether. To the product 200 ml dichloromethane is added and the mixture is refluxed for 2 h. The mixture is filtered and washed with dichloromethane. The solvent of the filtrate is distilled off. Colum chromatog10 raphy on silica gel with toluene/ethyl acetate 19/1 gave the product 6.47 g (22 %).1H NMR (400 MHz, DMSO-d6): = 8.32 (t, J =1.8 Hz, IH), 8.19-8.24 (m, 2H), 7.93-7.96 (m,IH) 7.86-7.88 (m, IH), 7.63-7.68 (m 2H), 7.38-7.49 (m, 3H), 7.28-7.36 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; STENGEL, Ilona; HEINEMEYER, Ute; NAGASHIMA, Hideaki; BARDON, Kristina; WO2015/150234; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39021-62-0, 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 39021-62-0 as follows.

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (Intermediate 12: step d, 3.0 g, 6.97 mmol) was added THF (40 ml) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to dryness to give the title compound.

According to the analysis of related databases, 39021-62-0, 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; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, These common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-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.

A solution of n-BuLi (2.5 M in hexanes, 0.24 mL, 0.6 mmol) was added dropwise by syringe to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (107.8 mg, 0.616 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.217 g, 0.512 mmol, Intermediate 46: step b) in dry THF (2 mL) was added to the mixture via syringe. After 5 minutes, the reaction was removed from the cold bath and was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound. 1H NMR (400 MHz, CDCl3) delta 8.23 (d, J=2.2 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H), 7.37 (dd, J=8.8, 2.1 Hz, 1H), 7.30-7.25 (m, 2H), 6.97-6.92 (m, 2H), 6.19 (s, 1H), 6.12 (s, 2H), 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [M+H]+.

Statistics shows that 5-Bromo-1,2-dimethyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 24134-09-6.

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; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem