Category: 16681-59-7

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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-1-methyl-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

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:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-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. Recommanded Product: 2-Bromo-1-methyl-1H-imidazole

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-1-methyl-1H-imidazole

Step 2 To a 500 mL round flask was added N-methyl-2-bromoimidazole (6.50 g, 40 mmol),2,4-diflurophenylboronic acid (7.89g, 50 mmol), palladium(II) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME and 100 mL of water. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours. The mixture was extracted with ethyl acetate and further purified by a silica gel column. Distillation of the product at 150 C. gave N-methyl-2-(2,4-difluorophenyl)imidazole as a colorless oil (6.60 g, 85% yield), characterized by 1H-NMR and MS.

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; Lin, Chun; Ma, Bin; Knowles, David B.; Brooks, Jason; Kwong, Raymond; US2006/8670; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-59-7, 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. 16681-59-7 name is 2-Bromo-1-methyl-1H-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.

[0461] 2-(2-chlorophenyl)-4-(piperazine-l-yl)quinazoline (91 mg, 0.281 mmol) was dissolved in NMP (3 mL) in a microwave reactor vial. Then 2-bromo-l- methylimidazole (0.05 mL, 0.561 mmol) was added and the mixture heated at 200 0C for 10 minutes in a microwave reactor. The mixture was poured into H2O, extracted with CH2Cl2, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was then purified by reverse phase HPLC (10% – 90% MeCNZH2O) to give the title compound. 1U NMR (400 MHz, CDCl3) delta 8.23 (m, IH), 8.13 (m, IH), 8.02 (m, IH), 7.92 (m, 2H), 7.67 (m, IH), 7.46 (m, 2H), 7.16 (d, IH), 6.83 (d, IH), 4.32 (m, 4H), 3.69 (m, 5H), 3.39 (m, 2H). MS (M/z, M+l), 405.5.

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

Some common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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. Application In Synthesis of 2-Bromo-1-methyl-1H-imidazole

To a solution of 2-bromo-1-methyl-1H-imidazole (9) (0.10 g, 0.60 mmol) in dry toluene (6 mL), p-anisidine (0.15 g, 1.19mmol), Pd2(dba)3 (51.02 mg, 0.06 mmol), BINAP (0.11 g, 0.18 mmol) and Cs2CO3 (0.39 g, 1.19mmol) were added sequentially, and the resulting mixture was heated at 100 C for 21 h. Thereaction was quenched by the addition of saturated NaHCO3 (5 mL). The organic layer wasseparated and the aqueous phase was extracted with AcOEt (3 × 10 mL). The combined organicextracts were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo, to obtain 10(0.11 g, 90 %) as an oil. This product was unstable and could not be further purified by columnchromatography: IR (film): numax 3343 cm-1; 1H NMR (300 MHz) delta 3.44 (broad s, 1H), 3.55 (s,3H), 3.70 (s, 3H), 6.67 (d, J 9.0 Hz, 2H), 6.72 (d, J 9.0 Hz, 2H), 6.92 (d, J 1.4 Hz, 1H), 6.97 (d, J1.4 Hz, 1H); 13C NMR (75.5 MHz) delta 34.3, 55.5, 114.6, 116.1, 119.8, 122.8, 129.5, 139.9, 152.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-59-7, its application will become more common.

Synthetic Route of 16681-59-7, 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. 16681-59-7 name is 2-Bromo-1-methyl-1H-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 flask was charged with tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.90 g, 5.47 mmol, 1.1 eq), 2-bromo-1-methyl-imidazole (800 mg, 4.97 mmol, 1 eq), (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) dichloride (181 mg, 0.24 mmol, 0.05 eq), sodium carbonate (1.05 g, 9.94 mmol, 2 eq), dioxane (18 mL) and water (3 mL). The mixture was purged with nitrogen for 5 mins and heated to 110 C. for 12 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL*3). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuum. The crude residue was purified by column chromatography (petroleum ether:ethyl acetate=1:0 to 3:1). Tert-butyl N-[(1S)-1-[4-(1-methylimidazol-2-yl)phenyl]ethyl]carbamate (850 mg, 2.82 mmol, 56% yield) was obtained as a grey solid.

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

Adding a certain compound to certain chemical reactions, such as: 16681-59-7, name is 2-Bromo-1-methyl-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 16681-59-7, Formula: C4H5BrN2

General procedure: To degassed DMF (8.0 mL) was added Pd(dppf)Cl2 (73 mg, 0.10 mmol), bis(pinacolato)diboron (508 mg, 2.0 mmol), potassium acetate (589 mg, 6.0 mmol), and 2,6-dibromobenzene (0.121 mL, 236 mg, 1.0 mmol) in order at room temperature. The mixture was heated to 130 C for 1 hour to complete formation of the boronic ester. Then 3-bromopyridine (0.289 mL, 474 mg, 3.0 mmol) and degassed aqueous sodium hydroxide (2.00 mL, 3.0 M, 6.0 mmol) were sequentially added to the hot reaction, and heating at 130 C was continued for another 3 hours when the reaction was complete (by GCMS). The reaction was cooled and evaporated to a residue in vacuo. The residue was extracted with chloroform, and the combined extracts were concentrated and applied to preparative silica TLC plates. After development by 1:1 THF:EtOAc the product bands were removed and extracted with DME. Evaporation of extract solutions resulted in the yields. The products could be purified by sublimation at 180 C and 10 mmHg if needed.

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

Reference:
Article; Avitia, Bertoldo; MacIntosh, Eric; Muhia, Samuel; Kelson, Eric; Tetrahedron Letters; vol. 52; 14; (2011); p. 1631 – 1634;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16681-59-7, name is 2-Bromo-1-methyl-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 16681-59-7, HPLC of Formula: C4H5BrN2

Similarly, compound f1 (6.05 g, 37.6 mmol)Dissolved in tetrahydrofuran (140 mL),Adding hexane solvent and dropping at -78 CAfter 2.5 M n-butyllithium (18 mL, 45.1 mmol),Stir for 1 hour.Then slowly add trimethyl borate (13 mL, 56.4 mmol)After that, stir for 2 hours.Then add 2M hydrochloric acid to neutralize,The product was extracted with ethyl acetate and water.Recrystallization from dichloromethane and hexane gave compound g1 (3.56 g, 77%).Weighed compound g1 (3.16 g, 25.1 mmol),Compound e1 (6.23 g, 25.1 mmol),Tetrakistriphenylphosphine palladium (11g, 10mmol)And potassium carbonate (8.42 g, 60.9 mmol),The weighed reactant was dissolved in toluene (1 L) / EtOH (200 mL) / distilled water (200 mL)The solvent was heated at 90 C for 2 hours.After the reaction is completed, the pressure is concentrated,Extract with ethyl acetate and concentrate.Column chromatography gave Intermediate A1 (4.07 g, 65%).

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; Changchun Hai Purunsi Technology Co., Ltd.; Han Chunxue; Cai Hui; (33 pag.)CN108676034; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Synthesis of 1-(1-methyl-1H-imidazol-2-yl)piperazine 1.0 g (6.2 mmol) 2-bromine-1-methyl-1H-imidazol was fused with 3.2 ml (37.0 mmol) piperazine at 145 C. and stirred for 18 h at this temperature. After cooling to RT, the residue was received in 10% aq. hydrochloric acid and washed with AE. Alkalic adjustment was subsequently performed with a 10% aq. NaOH sol. (pH>12) and extraction with DCM. The organic phase was dried over MgSO4, filtered and concentrated in a vacuum. In this process, 780 mg (4.7 mmol, 76%) 1-(1-methyl-1H-imidazol-2-yl)piperazine was obtained.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2008/261996; (2008); A1;,
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 16681-59-7 as follows. Computed Properties of C4H5BrN2

Step 3: 7-Chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine (7); To a solution of the tin derivative 6 (24.79 g, 54.05 mmol) and 2-bromo-1-methyl-1H-imidazole (10.4 g, 64.86 mmol) [McCallum, P. W.; Weavers, R. T.: Grimmet, M. R.; Blackman, A. G.; Aust. J. Chem.; 52; 3; 1999; 159-166.1 in toluene (180 mL) Pd[PPh3]4 (5 g, 4.32 mmol) was added and the mixture was refluxed under nitrogen for 2 days, cooled to room temperature. A precipitate was formed which was collected by filtration, washed with Et2O and dried, to afford the title compound 7 as a grey solid (12.72 g, 94% yield). MS (m/z): 250.0 (M+H).

According to the analysis of related databases, 16681-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Methylgene, Inc.; US2007/4675; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem