Category: 1003-21-0

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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a solution of 5-bromo-1-methylimidazole (0.68 g, 4.26 mmol) in dry DCM (15 mL), DIPEA (0.77 mL, 4.47 mmol) and iPrMgCl (2.13 mL, 4.26 mmol, 2.0 M solution in THF) was added at 10 C. The reaction mixture was stirred for 1.5 h and a solution of compound J (0.5 g, 1.06 mmol) in DCM was added to it. The reaction mixture was refluxed for 2 h and quenched with saturated NH4Cl solution. The product was extracted with DCM (30 mL). The organic layer was dried, filtered and concentrated to give crude c. Purification of the crude product provided 210 mg (36%) of compound K.1H NMR (400 MHz, CDCl3): delta 0.27 (s, 9H), 3.38 (s, 3H), 3.78 (s, 3H), 6.28 (s, 1H), 6.64 (s, 1H), 7.11 (d, J=7.6 Hz, 1H), 7.22 (s, 1H), 7.24 (s, 1H), 7.29 (s, 1H), 7.30-7.36 (m, 3H), 7.37 (s, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H), 8.57 (d, J=5.0 Hz, 1H); LCMS m/z: 553 (M+1).

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 1003-21-0.

Reference:
Patent; Link Medicine Corporation; US2010/130540; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1,3-Benzenediboronic acid (300 mg, 1.8 mmol), 5-bromo-1-methylimidazole (291 mg, 1.8 mmol), potassium phosphate (1.15 g, 5.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (164 mg, 0.18 mmol), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (142 mg, 0.36 mmol) were combined with DMA (3 mL) in a sealed tube purged with N2. The reaction was heated at 130 C. for 25 min in a microwave reactor. The solution was diluted with MeOH, filtered, and concentrated in vacuo. Purification by preparatory HPLC gave 166 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.12 (s, 1H), 7.91-7.98 (m, 2H), 7.83 (s, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 3.83 (s, 3H). [M+H] calc’d for C10H11BN2O2, 202; found, 202

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dong, Qing; Hosfield, David J.; Paraselli, Bheema R.; Scorah, Nicholas; Stafford, Jeffrey A.; Wallace, Michael B.; Zhang, Zhiyuan; US2006/84650; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-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.

To a flask containing 5-bromo-1-methyl-1H-imidazole (650 mg, 4.04 mmol) was added THF (10 mL) and the clear homogeneous solution was stirred at room temperature as iPrMgCl (2 M in diethylether, 2 mL, 4 mmol) was added. A whitish suspension resulted. The suspension was stirred at room temperature for 30 minutes, then a solution of 4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (660 mg, 1.36 mmol, Intermediate 81: step b) in THF (5 mL) containing LaCl3-LiCl complex (0.5 M solution THF, 5 mL, 2.5 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at 35 C. After 14 hours, the reaction mixture was quenched with saturated aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*40 mL) and the combined organics were washed with brine and dried over MgSO4. The brine portion was back-extracted with DCM (3*40 mL) and dried over MgSO4. The organics were filtered and concentrated to dryness to afford a tan oil. The residue was purified by FCC (2% MeOH-DCM increasing to 10% MeOH) to provide the title compound as an off white solid. 1H NMR (500 MHz, CDCl3) delta 8.13 (d, J=2.0 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.44-7.35 (m, 4H), 7.31 (d, J=11.4 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.90 (d, J=8.0 Hz, 1H), 6.19 (s, 1H), 4.67 (s, 1H), 4.32 (s, 2H), 4.07 (s, 3H), 3.46 (s, 3H), 2.52 (s, 3H), 2.45-2.33 (m, 3H); MS (ESI): mass calcd. Chemical Formula: C30H26ClF3N4O2, Exact Mass: 566.2. m/z found 567.1 [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 5-Bromo-1-methyl-1H-imidazole, 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; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-21-0, 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 1003-21-0 as follows.

iPrMgCl (2.06 M in THF, 0.72 mL, 1.48 mmol) was added dropwise at 0 C. over 1.5 minutes to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (0.257 g, 1.60 mmol) in THF (4 mL; dried over 3 A molecular sieves) under argon. After stirring for 17 minutes, a solution of tert-butyl 4-(4-chloro-2-methoxy-3-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-6-carbonyl)piperidine-1-carboxylate (0.452 g, 0.899 mmol, Intermediate 5) and LaCl3-2LiCl (0.5 M in THF, 1.98 mL, 0.988 mmol) in THF (2 mL) was added dropwise over 2 minutes to the Grignard reagent at 0 C., and after 30 minutes the reaction was quenched with 5 M aqueous NH4Cl (1 mL). The aqueous layer was extracted with DCM (1*5 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by FCC (0-10% MeOH in DCM) to afford the title compound as a white foam. 1H NMR (400 MHz, CDCl3) delta 8.10 (br. s., 1H), 7.74 (d, J=8.59 Hz, 1H), 7.34-7.41 (m, 1H), 7.29 (s, 1H), 7.18 (s, 1H), 4.25 (br. s., 1H), 4.07 (s, 3H), 3.91-3.98 (m, 2H), 3.28-3.38 (m, 2H), 3.23 (s, 3H), 2.90 (d, J=7.07 Hz, 2H), 2.55-2.85 (m, 2H), 2.31-2.42 (m, 1H), 2.18-2.26 (m, 1H), 1.91-2.04 (m, 1H), 1.66 (br. s., 3H), 1.49-1.59 (m, 3H), 1.41 (s, 9H), 1.29-1.38 (m, 1H), 1.13-1.23 (m, 2H); MS m/e 584.8 [M+H]+.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 73: 2-methoxy-4-(1 -methyl-1 – -imidazol-5-yl)aniline Method F A suspension of 5-bromo-1 -methyl-1 H-imidazole (228 mg, 1.42 mmol), 2- methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (423 mg, 1 .70 mmol), Pd(PPh3)4 (164 mg, 0.142 mmol) and CsF (645 mg, 4.25 mmol) in DME/MeOH (9/3 mL) was stirred at 150^ under microwave irradiation for 60 minutes. The reaction mixture was filtered and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with between 0-4% MeOH in EtOAc to afford the title compound (137 mg, 48%). 1 H NMR (500 MHz, CDCI3): delta 7.56 (s, 1 H), 7.02 (s, 1 H), 6.81 – 6.76 (m, 3H), 3.95 (s, broad, 2H), 3.88 (s, 3H), 3.64 (s, 3H). LCMS (ESI) Rt = 0.43 minutes MS m/z 204 [M+H]+

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-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.

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give 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, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-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.

General procedure: Ethyl 2-chloro-2-oxoacetate (8.19 g, 60.0 mmol) was added dropwise over 20 min to the corresponding imidazole (60.0 mmol) in CH2Cl2 (500 mL) at -20 C. Then, DIPEA (7.75 g, 10.5 mL, 60.0 mmol) was added at -20 C, the mixture was warmed up to rt and stirred for 12 h. The resulting mixture was washed with H2O (3 ¡Á 150 mL), the organic layer was dried over Na2SO4 and evaporated in vacuo [50]. 4.2.1 Ethyl 2-(5-bromo-1-methyl-1H-imidazol-2-yl)-2-oxoacetate (10h) (0013) Yield 15.0 g (96%); yellowish oil. 1H NMR (500 MHz, CDCl3) delta 7.32 (s, 1 H), 4.46 (q, J =7.1 Hz, 2 H), 4.02 (s, 3 H), 1.41 (t, J =7.1 Hz, 3 H). 13C NMR (126 MHz, CDCl3) delta 176.5, 163.2, 140.9, 132.6, 114.8, 62.6, 33.9, 14.0. LC/MS (CI): m/z = 261/263 [M+H]+. Anal. Calcd. for C8H9BrN2O3: C 36.80; H 3.47; N 10.73; Br 30.61. Found: C 36.66; H 3.65; N 10.58; Br 30.53.

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

Reference:
Article; Geraschenko, Oleksandr V.; Solomin, Vitalii V.; Vashchenko, Bohdan V.; Khodakivskyi, Pavlo; Tolmachev, Andrey A.; Grygorenko, Oleksandr O.; Journal of Fluorine Chemistry; vol. 229; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-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.

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 (801 mg, 4.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 5-bromo-1-methylimidazole (644 mg, 4.00 mmol) in 1 ,4-dioxane (30 ml) was added potassium phosphate (4246 mg, 20.00 mmol), trans- N,N-dimethylcyclohexane-1 ,2-diamine (0.631 ml, 4.00 mmol) and copper(l) iodide (762 mg, 4.00 mmol) and the mixture stirred at reflux overnight. The reaction mixture was diluted with dichloromethane and filtered through celite. The filter pad was washed with dichloromethane and the filtrate was reduced under vacuum. The residue was re-dissolved in dichloromethane, washed with 0.880 ammonia (x2), water then brine and passed through a hydrophobic frit and the solution was concentrated 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-5-yl)-2-oxo-4- imidazolidinecarboxylate (393 mg, 32.6 % yield). LC/MS [M+H]+ = 281.

The synthetic route of 1003-21-0 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-1-methyl-1H-imidazole

intermediate 2: step c(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanoneTo a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo- 1 -methyl- 1 H-imidazole (47.96 g, 297.9 mmol), followed by TI1F (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1 .3 in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C in an ice bath. To this mixture was added a solution of N-methoxy-N-m.ethyl-6- (irifiuoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C with an ice bath and carefully quenched with 2 N aqueous HCl to pH = 7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phases split and the organic layer was washed with brine (2 x 200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and suspension was filtered to provide the title compound as a solid.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-21-0, 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 1003-21-0 as follows.

Intermediate 2: step c (1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanone To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo- 1 -methyl- lH-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropyimagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6- (trifluoromethyi)nicotinamide (53,66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C with an ice bath and carefully quenched with 2 N aqueous HC1 to pH = 7 (quenching temperature reached 12 C). The mixture was diluted with ethyl acetate (500 mL), phase split and the organic layer was washed with brine (2 x 200 mL) and dried over sodium sulfate, filtered, and the solvent was removed. Hot, ether was added and the mixture was filtered to give the title compound as a solid.

According to the analysis of related databases, 1003-21-0, 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; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem