Category: 24134-09-6

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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 24134-09-6, 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. 24134-09-6 name is 5-Bromo-1,2-dimethyl-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 solution of n-BuLi (4.0 mL, 10 mmol, 2.5 M solution in hexane) was slowly added to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (1.77 g, 10.2 mmol) in THF (70 mL) at -78 C. After addition, stirring was continued for an additional 30 minutes and N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (1.76 g, 10.1 mmol, Intermediate 1: step a, Procedure A) dissolved in THF (25 mL) was slowly added. An additional 6 mL of THF was used to complete the quantitative addition. The mixture was stirred at -78 C. for 5 minutes then warmed to room temperature and stirred for 1 hour. The solution was quenched with water and layers were separated. The aqueous layer was extracted with DCM and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 6% MeOH/DCM) to provide the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-dimethyl-1H-imidazole, and friends who are interested can also refer to it.

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

Some common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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 5-Bromo-1,2-dimethyl-1H-imidazole

Example 67: (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol 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-l ,2-dimethyl-lH-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- lH-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 (Na^SC ), 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, NMR (400 MHz, CDC13) 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, i l l). 7.30 – 7.25 (m, 2H), 6.97 – 6.92 (m, 21 1). 6.19 (s, 1H), 6.12 (s, 21 1). 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [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 24134-09-6, its application will become more common.

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

Some common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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 5-Bromo-1,2-dimethyl-1H-imidazole

Example 67: (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol 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-l ,2-dimethyl-lH-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- lH-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 (Na^SC ), 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, NMR (400 MHz, CDC13) 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, i l l). 7.30 – 7.25 (m, 2H), 6.97 – 6.92 (m, 21 1). 6.19 (s, 1H), 6.12 (s, 21 1). 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [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 24134-09-6, its application will become more common.

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

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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H7BrN2

A solution of 5-bromo-1,2-dimethyl- 1H-imidazole (10.6 g, 60.8 mmol) in THF (400 mE) was cooled to -77 C. Maintaining a temperature of<-70 C., nBuLi (27.7 ml, 72.0 mmol, 2.5 M in hexanes) was added over 10 mm. After 10 mm, a solution of (4-chloro-2-methoxy-3-(4-(trifluorom- ethyl)benzyl)quinolin-6-yl)(1 -methyl-i H-i ,2,3-triazol-5-yl)methanone (20.0 g, 43.4 mmol, Intermediate 63) inTHF (290 mE) was added over 10 mm maintaining a temperature of <-60 C. The reaction mixture was allowed to warm to 0 C. over 1 hand then quenched with aqueous ammonium chloride (500 mE, 13 wt %). The resulting layers were separated and the organic layer was washed with brine (400 mE). The organic layer was dried over Mg504, filtered, and concentrated. The residue was taken up in acetone (200 mE) and allowed to stir for 2 h. The resulting suspension was filtered and washed with acetone (20 mE). After drying in a vacuum oven at 60 C. the title compound was obtained as a white solid. ?H NMR (400 MHz, CDC13) oe ppm 8.24 (d, J=2.2 Hz, iH), 7.72 (d, J=8.7 Hz, iH), 7.54-7.47 (m, 3H), 7.42-7.33 (m, 3H), 7.06 (s, iH), 5.97 (s, iH), 4.32-4.22 (m, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.32 (s, 3H), 2.13 (s, 3H); MS mle 557.1 (M+H). (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl) quinolin-6-yl)(i ,2-dimethyl- 1 H-imidazol-5-yl)(i -methyliH-i,2,3-triazol-5-yl)methanol was resolved into its constituent enantiomers by chiral HPEC [Chiralcel OD, mobile phase: 85% heptane, 15% ethanol]. Afier resolution, the individual enantiomers were crystallized from acetone (7.5 mE/g) and isolated by filtration after the addition of heptane (15 mE/g). The first eluting enantiomer was Example 80B: ?H NMR (400 MHz, CDC13) oe ppm 8.23 (d, J=2.2 Hz, iH), 7.72 (d, J=8.8 Hz, iH), 7.51 (d, J=8.2 Hz, 2H), 7.43-7.33 (m, 3H), 7.05 (s, iH), 6.99 (bs, iH), 6.01 (s, iH), 4.30 (s, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.34 (s, 3H), 2.17 (s, 3H); MS mle 557.1 (M+H). The second eluting enantiomer was Example 80C:?H NMR (500 MHz, CDC13) oe ppm 8.19 (d, J=2.2 Hz, iH), 7.74 (d, J=8.7 Hz, iH), 7.52 (d, J=8.2 Hz, 2H), 7.43-7.35 (m, 3H), 7.14 (s, iH), 6.08 (s, iH), 5.32 (bs, iH), 4.33 (s, 2H),4.07 (s, 3H), 3.91 (s, 3H), 3.38 (s, 3H), 2.28 (s, 3H); MS mle557.1 (M+H). According to the analysis of related databases, 24134-09-6, 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

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, 5-Bromo-1,2-dimethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-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 24134-09-6, Safety of 5-Bromo-1,2-dimethyl-1H-imidazole

A solution of n-BuLi (2.66 M in hexane, 19.5 mL, 51.9 mmol) in THF (100 mL) was stirred under argon at ?-70 C. while a solution of 5-bromo-1,2-dimethyl-1H-imidazole (9.13 g, 52.2 mmol) in THF [60 mL; containing 3 A molecular sieves (18 g)] was added dropwise over 8 minutes via cannula. After stirring for another 4 minutes at ?-70 C., neat ethyl methoxy(methyl)carbamate (2.96 mL, 22.7 mmol) was added dropwise over 3 minutes. This mixture was stirred at ?-70 C. for an additional 5 minutes, and the cold bath was then removed and the slurry was allowed to warm to room temperature with stirring for 1.5 hours. The reaction was then quenched with 5 M aqueous NH4Cl (15 mL), dried (Na2SO4), filtered, and concentrated under high vacuum at 80 C. The resulting orange gummy residue was triturated with hot heptane (?40 mL) and the decanted supernatant was allowed to crystallize to provide impure title compound. This was recrystallized from toluene (?30 mL) to provide, after washing the off-white crystalline filter cake with toluene (2*?3 mL), the title compound as an off-white crystalline solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-dimethyl-1H-imidazole, and friends who are interested can also refer to it.

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

Reference 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 mixture of {3-chloro-5-[(methyloxy)carbonyl]phenyl}boronic acid (1.703 g, 7.94 mmol), 4-bromo-1 ,2-dimethyl-1 H-imidazole (D37a, 1.1 12 g, 6.35 mmol) and 5- bromo-1 ,2-dimethyl-1 H-imidazole (D37b, 222 mg, 1.271 mmol) as an isomeric mixture, sodium carbonate (1.347 g, 12.71 mmol) and bis(triphenylphosphine)palladium(ll) dichloride (446 mg, 0.635 mmol) in toluene (10 ml.) and ethanol (1 ml.) was stirred under reflux overnight. The reaction mixture was partitioned between dichloromethane and water and the layers separated. The aqueous layer was extracted with dichloromethane (x2) and the combined organic layers were dried (magnesium sulfate) and concentrated. The residue was acidified and purified using SCX chromatography, eluting with methanol then 2N ammonia in methanol. The basic fractions were combined and concentrated to leave the crude mixture of title compounds which was used without further purification. LC/MS (ES+ve): [M+H]+ 265, 267 (Ci3H13CIN2O2 requires [M+H]+ 265, 267)

The synthetic route of 24134-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/819; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 163: 4-(1 ,2-dimethyl-1 H-imidazol-5-yl)aniline; [00335] Tetrakis(triphenylphosphine)palladium (0.053g, 0.046mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.456mmol), 5- bromo-1 ,2-dimethyl-1 /-/-imidazole (0.088g, 0.502mmol) and cesium fluoride (0.208g, 1 .369mmol) in DME/MeOH (2/1 , 2.9ml_). The reaction mixture was heated for 10 minutes at ~ 50 C under microwave irradiation. The reaction was diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified using Biotage silica gel column chromatography eluting with 1 to 5% MeOH/aq. NH3 (10/1 ) in DCM followed by filtration through a SCX-2 column to afford the title product as a white solid (48mg, 56%).1 H NMR (500MHz, CDCI3): delta 2.42 (s, 3H), 3.46 (s, 3H), 3.81 (br s, 2H), 6.71 -6.74 (m, 1 H), 6.85 (s, 1 H), 7.12-7.14 (m, 1 H).LC (Method B)-MS (ESI, m/z) fR 0.24 min, 188 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,2-dimethyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); 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 24134-09-6 as follows. COA of Formula: C5H7BrN2

n-BuLi (2.66 M in hexanes, 0.963 mL, 2.56 mmol) was added dropwise to a stirred slurry of 5-bromo-1,2-dimethyl-1H-imidazole (470 mg, 2.68 mmol) in THF (7 mL) at ?-70 C. under argon. After stirring for another 7 minutes, the slurry was treated dropwise over 5 minutes with a solution of methyl 4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carboxylate (500 mg, 1.22 mmol, Intermediate 75) in THF (6 mL). The reaction was stirred in the dry ice/acetone bath for another 10 minutes, then removed from the cold bath and stirred for 6 minutes, then stirred in an ice bath for 2 minutes, then quenched with 5 M aqueous NH4Cl (0.77 mL, 3.85 mmol) to give an orange solution. The reaction mixture was dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified by silica flash column chromatography (0-10% MeOH/DCM) to provide the title compound.

According to the analysis of related databases, 24134-09-6, 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