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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7BrN2

[0003901 To a stirred solution of compound 1 (0.2 g, 1 eq) in aq. ammonia solution (2 mL), copper chloride (catalytic amount) was added and heated at 100 °C for 5 h in a sealed tube. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20percent methanol in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to afford title compound 2. LCMS (mlz): 148.00 (M + 1).

The synthetic route of 53484-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1219741-19-1, 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. 1219741-19-1 name is 5-Chloro-6-iodo-2-(methylsulfonyl)-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.

A solution of potassium phosphate, tribasic (2 M solution in water; 21 mL, 42 mmol), Pd(PPh3)4 (0.324 g, 0.280 mmol), 4-biphenylboronic acid (3.94 g, 1 .9 mmol) and 6-chloro-5-iodo-2- (methylsulfonyl)-lH-benzimidazole (Intermediate 1, 5 g, 14 mmol) in dioxane (70 mL) was heated at 100C for 5 h. The aqueous phase was removed and the organic phase wasconcentrated, diluted with EtOAc and DCM, and filtered. The filtrate was concentrated to afford the desired product as a white solid, which was used in the next step without further purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JIANG, Jinlong; KASSICK, Andrew, J.; KEKEC, Ahmet; SEBHAT, Iyassu, K.; WO2011/106273; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, 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. Recommanded Product: 18075-64-4

DMSO (0.5 mL) was added to a mixture of 1-phenyl-1H-imidazole-4-carboxylic acid (34 mg, 0.18 mmol) and 1-pyrrolo[1,2-c]pyrazin-1-yl-pyrrolidin-3-ylamine dihydrochloride salt (50 mg, 0.18 mmol). To this was added triethylamine (0.100 mL, 0.72 mmol) followed by HATU (76 mg, 0.20 mmol). The mixture was allowed to stir for 30 min after which time it was diluted with dichloromethane (1.0 mL), washed with water (3*1.0 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC (10:90-95:5 MeCN:H2O+0.1% TFA). The combined product fractions were lyophilized to give the TFA salt of the product as a pale yellow solid (49 mg, 0.10 mmol, 56% yield).

The synthetic route of 1-Phenyl-1H-imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a three-necked flask equipped with a stirrer and a thermometer, 1.44 g (8.0 mmol) of N-octylimidazole, 0.56 g (4.4 mmol) 1,3-dichloro-2-propanol, stirring at 115 ° C ~ 125 ° C reaction, TLC follow the progress of the reaction, about 8 ~ 12h after the end of the reaction. The crude product was recrystallized from a mixed solvent of chloroform and ethyl acetate, A white powdery solid was obtained 1,1 ‘-dioctyl-3,3′(2-hydroxy-1,3-propylene) imidazole hydrochloride (1.02 g, yield 52.1percent).

The synthetic route of 1-Octyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qiqihar university; Wang, LiYan; Deng, QiGang; Zheng, YongJie; Huo, shichao; Liu, Jia; Sun, zhu; (10 pag.)CN103951702; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2, A common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

6.02.05.01 (2,4,5-tribromo-imidazol-1-yl)-acetic acid methyl ester 5.1 mL methyl bromo acetate was added to 15 g 2,4,5-tribromoimidazole and 20.4 g potassium carbonate in 100 mL DMF. The reaction was stirred 3 h at RT. The mixture was added to water. The precipitate was filtered, washed with water and dried to give 18.1 g desired product. Rt: 0.93 min (method B), ESI+: 375

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUDOLF, Klaus; BISCHOFF, Daniel; DAHMANN, Georg; GRAUERT, Matthias; KUELZER, Raimund; US2013/150355; (2013); 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 39021-62-0

Example 2: (2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanoln-BuLi (2,5 M in hexanes, 0,52 mL, 1 .3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-phenylquinoline (353 mg, 1 mmol, intermediate 1 : step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed up to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2 x 50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1 :5) to afford the title compound as a white solid. MS (ESI): 384.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.45 (s, 1H), 7.94 (dd, J = 42.2, 8.0 Hz, 2H), 7.73-7.24 (m, 6H), 6.56 (s, 1H), 6.16 (s, 1H), 3.70 (s, 3H).

The synthetic route of 39021-62-0 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.; WO2015/57206; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-56-4, The chemical industry reduces the impact on the environment during synthesis 16681-56-4, name is 2-Bromo-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step 1. 2-Bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (0910) [00290] A mixture of 2-bromo-lH-imidazole (20 g, 136.99 mmol) and potassium carbonate (56.71 g, 410.97 mmol) in acetone (200 mL) was treated by the dropwise addition of (2- (chloromethoxy)ethyl)trimethylsilane (27.29 g, 164.39 mmol) and the resulting mixture was stirred for 3 h at ambient temperature. The reaction mixture was filtered, concentrated under vacuum and the residue was purified by silica gel chromatography (eluting with a gradient of 1- 10% EtOAc/PE) to afford 30 g (80%) of 2-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazole as a colorless oil. MS (ESI) m/z 277 [M+H]+

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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. Application In Synthesis of 1-Methyl-1H-imidazole-2-carboxylic acid

A mixture of 5-methyl-2- (2-pyridyl)-5 ,6,7 ,8-tetrahydropyrido [4,3 d]pyrimidine trifluoroacetic acid salt (100 mg, 442 imol, the product of step 2 in Example 34), 1- methylimidazole-2-carboxylic acid (83.6 mg, 663 j.imol), HATU (336 mg, 884 imol) and DIPEA (171 mg, 1.33 mmol) in DMF (5 mL) was stuffed overnight at rt. The resulting mixturewas poured into water and extracted with DCM (30 mL) twice. The combined organic layer was concentrated in vacuo and the residue was purified by prep-HPLC to give (1-methylimidazol-2- yl)- [5-methyl-2- (2-pyridyl)-7 ,8 -dihydro-5H-pyrido [4,3-d]pyrimidin-6-yl] methanone (69 mg) as a light yellow solid. ?H NMR (400 MHz, Methanol-d4) oe: 8.5 1-8.80 (m, 2H), 8.33-8.43 (m, 1H), 7.80-7.92 (m, 1H), 7.34-7.47 (m, 1H), 7.07-7.18 (m, 1H), 6.97 (d, 1H), 5.66-5.86 (m, 1H), 4.66-4.75 (m, 0.4H), 4.49-4.60 (m, 0.6H), 3.74 (s, 3H), 3.48-3.63 (m, 0.7H), 3.23-3.41 (m, 1H), 2.88-3.15 (m, 1.3H), 1.56 (brd, 3H). MS obsd. (ESI)[(M+H)]: 335.

The synthetic route of 20485-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (84 pag.)WO2018/83106; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 36947-68-9, These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-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.

General procedure: A solution of imidazole 4-13, benzimidazole 40, 41, pyridoimidazole 42 or benzotriazole 43 (23 mmol) in dry DMF (15 mL) and K2CO3 (11.5 mmol) was stirred for 10 min at 0-5 C, under nitrogen atmosphere. After this time, appropriate 1-aryl-2-bromo-ethanone 18-21 (23 mmol) was added and the mixture was stirred for 1.5 h then poured into ice water. The resulting crude material was extracted with dichloromethane (3 × 50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure; the obtained residue were purified by means of flash chromatography performed using silica gel 60 (230-400 mesh) and a mixture of ethyl acetate/methanol 8:2 v/v or dichloromethane/methanol 9.5/0.5 v/v (only for purification of 25 and 26, 49 and 51, 50 and 52, respectively) as eluent.

Statistics shows that 2-Isopropyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 36947-68-9.

Reference:
Article; Salerno, Loredana; Modica, Maria N.; Romeo, Giuseppe; Pittala, Valeria; Siracusa, Maria A.; Amato, Maria E.; Acquaviva, Rosaria; Di Giacomo, Claudia; Sorrenti, Valeria; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 118 – 126;,
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. 1072-63-5, name is 1-Vinyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H6N2

1-vinyl imidazole (5.18 g, 55 mmol) and 1,6-dibromohexane (2.79 g, 22 mmol) were dissolved in methanol (50 mL) in a round-bottom flask fitted with a condenser and N2 bubbler. Subsequently, the mixture was stirred at 80 C for 48 h under a nitrogen atmosphere. After then, the reaction mixture was precipitated from diethyl ether (150 mL), and recrystallized twice from diethyl ether. The products were dried under vacuum for 24 h at R.T. [C6VIm]Br was obtained as white solid. Yield: 71%. [C6VIm]Br: 1H-NMR (D2O, 400 MHz, ppm):7.57 (1H, s); 7.37 (1H, s); 6.93 (1H, m); 5.60 (1H, d); 5.22 (1H, d); 4.04 (2H, t); 1.70 (2H, s); 1.17 (2H, s).1H-NMR (DMSO, 400 MHz, ppm): 9.66 (1H, s); 8.24 (1H, t); 7.99 (1H, t); 7.33 (1H, m); 5.99 (1H, m);5.43 (1H, m); 4.22 (2H, t); 1.83 (2H, d); 1.31 (2H, s). 13C-NMR (DMSO, 100 MHz, ppm): 135.36,128.88, 123.31, 119.23, 109.04, 49.02, 28.80, 24.77. ESI-MS (m/z): calcd. for C16H24N4Br2: 432.2,found: 432.2. Elemental analysis (%): Calculated: C, 44.46; H, 5.60; N, 12.96; Br, 36.98. Found: C,42.94; H, 5.36; N, 12.50; Br, 39.20. M.P.: 219 C.

The synthetic route of 1072-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Liu, Jingjiang; Zuo, Yong; Wang, Rongmin; Xiong, Yubing; Molecules; vol. 20; 9; (2015); p. 17378 – 17392;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem