Category: 1003-21-0

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., category: imidazoles-derivatives

Intermediate 55: step b bis(1-methyl-1H-imidazol-5-yl)methanone To a solution of 5-bromo-l -methyl- IH-imidazole (1.2 g, 7.45 mmol) in DCM (10 mL) was added ethyl magnesium, bromide (2.5 mL, 7.45 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting pale yellow solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C and then N-methoxy-N, 1 -dimethyl- lH-imidazole-5- earboxamide (1.0 g, 6.21 mmol, Intermediate 55: step a) dissolved in DCM (3 mL) was added dropwise. The cold bath was removed and the reaction mixture stirred at room temperature for 48 hours. To the resulting yellow suspension was added water followed by 6 M aqueous HCl to a neutral pH (pH = 6 – 7). The aqueous mixture was extracted with DCM (2 x). The combined DCM extracts were dried over MgS0 , filtered and concentrated under reduced pressure. The product was precipitated with Et20, filtered and dried to provide the title compound as a tan solid.

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; 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

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. Recommanded Product: 1003-21-0

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M] (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-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 15, 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 2N HCl to a 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¡Á200 mL) and dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and then 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-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 1003-21-0, name: 5-Bromo-1-methyl-1H-imidazole

[0206] A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 19.5 mE, 25.35 mmol) was added dropwise by syringe to a solution of 5-bromo-1-me- thyl-1H-imidazole (4.12 g, 25.58 mmol) in dry THF (130 mE) at 0 C. After 15 minutes, the Grignard solution was added via cannulation to a solution of picolinaldehyde (2.0 ml, 20.93 mmol) in dry THF (55 mE) at 0 C. The reaction mixture was stirred for 5 minutes at 0 C., then warmed to room temperature for 1 hour. The reaction mixture was then cooled in an ice bath and quenched with saturated aqueous ammonium chloride. The mixture was partitioned between brine and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate. The organic phase was dried (Na2504), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) to provide the title compound as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-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.; US2015/105365; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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 mixture of 5-bromo-1-methyl-1H-imidazole (569 mg, 3.417 mmol) in THF (14 mL) at 0 C. was added iPrMgCl-LiCl (1.3 M in THF, 2.48 mL, 3.22 mmol) to provide a white suspension. This mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the mixture stirred at room temperature for 10 minutes. The reaction was then cooled to 0 C. in an ice-water bath and stirred at 0 C. for an additional 10 minutes. Then, a solution of 4-(3-(benzyloxy)-4-chloro-2-methoxyquinoline-6-carbonyl)benzonitrile (335 mg, 0.78 mmol, Intermediate 83: step a) in THF (8 mL) was added. The flask was rinsed with THF (1.5 mL), which was also added to the reaction. The resulting mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the reaction was allowed to stir at room temperature for 4 hours. The reaction was quenched by the addition of water (15 mL). The aqueous was then extracted with EtOAc (3*20 mL). The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness. The residue was triturated with Et2O, filtered and dried under air to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.01-7.99 (m, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.68-7.65 (m, 2H), 7.56-7.53 (m, 3H), 7.53-7.52 (m, 1H), 7.50-7.46 (m, 2H), 7.41-7.34 (m, 3H), 6.45-6.44 (m, 1H), 5.16 (s, 2H), 4.15 (s, 3H), 3.39 (s, 3H). MS (ESI): mass calcd. for C29H23ClN4O3, 510.2. m/z found, 511.0 [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; 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

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. Recommanded Product: 5-Bromo-1-methyl-1H-imidazole

To a solution of 153.3 (2.5g, O.76mmol, 1.Oeq) and5-bromo-1-methyl-1H-imidazole (1.5g, O.92mmol, 1.2eq) in a mixture of 1,2-dimethoxyethane (2OmL) and water (5mL), sodium carbonate (2.4g, 2.3mmol, 3.Oeq) was added. Reaction mixturewas degassed with argon for 15mm. Then [1,1?-Bi s(diphenylphosphino)ferrocene]di chloropalladium(II) complex with CH2C12 (0. 9g, 0. O7mmol, O.leq) was added and again degassed for 5mm. Reaction mixture was stirred at 115 C for 2h. After completion of the reaction, the reaction mixture was transferred into water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. This was purified by column chromatography using 2% MeOH in CH2C12 to obtain pure 212.1 (1.3g, 60.50%). MS(ES): m/z 281.57 [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; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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 1003-21-0. 1003-21-0

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium 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-(trifluoromethyl)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*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.

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 5-Bromo-1-methyl-1H-imidazole.

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.; US2015/105404; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life. 1003-21-0

Pd(PPh3)4 (55.9 mg, 48.4 mumol) was added to a mixture of 6 (300 mg, 0.484 mmol) and 5-bromo-1-methylimidazole (312 mg, 1.94 mmol) in aqueous Na2CO3 (2 M, 1.0 mL, 2.0 mmol) and anhydrous THF (9.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (25 mL), and the mixture was extracted with CHCl3 (50 mL¡Á3). The organic layer was washed with water (25 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 1 (150 mg, 59%) as a bluish white solid. Mp: 188.7-189.1 C. IR (KBr, cm-1): 1339, 1276, 1185, 1110, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.51 (s, br, 2H, ArH), 7.15 (d, J=1.1Hz, 2H, ArH), 7.00 (s, 2H, ArH), 3.68 (s, 6H, NCH3), 2.02 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 139.8, 129.7, 129.3, 125.7, 125.6, 125.4, 32.7, 14.4. MS (ESI+): m/z=529 [M+H]+. Anal. Calcd for C23H18F6N4S2: C, 52.27; H, 3.43; N, 10.60. Found: C, 52.03; H, 3.46; N, 10.54.

The chemical industry reduces the impact on the environment during synthesis 1003-21-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 2-(methylthio)-4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline (2. 8g, 1.05? mmol, 1. Oeq) and 5-bromo- 1-methyl- 1H- imidazole 1.1 (2.5g, 1 .58mmol, 1 .5eq.) in a mixture of dioxane (24mL) and water (6mL). Reaction mixture was degassed with argon atmosphere for 10mm. Then [1,1?- Bi s(diphenylphosphino)ferrocene]palladium(II) dichloride(0 .25 Og, 0.31 mmol, 0.03 eq) and potassium carbonate(4.3 7g,3. l6mmol,3eq) was added into it. Reaction mixture was stirred at 115c for 24h. Upon completion, reaction mixture was transferred into cold water then extracted with ethyl acetate. Organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 5% ethyl acetate in hexane as eluant to obtain pure 214.1 (1 .5g, 90.69 %). MS(ES): m/z 220.31 [M+H].

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

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-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 1003-21-0.

Intermediate 66: step b (1-methyl-1H-imidazol-5-yl)(pyrimidin-2-yl)methanone 5-Bromo-l-m.ethyl-lH-im.idazole (6.66 g, 41 ,4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2atmosphere. The contents were cooled to 0 C in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and the contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 66: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C, then slowly warmed to room temperature, then heated to 40 C in an oil bath for approximately 36 hours. The contents were then cooled to 0 C, quenched with a saturated aqueous NH4CI solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgS04, filtered, then distilled under reduced pressure to yield an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM / (10% of a 2 M N MeOH in DCM)) to provide the title compound.

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

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

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-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 1003-21-0.

5-Bromo-1-methyl-1H-imidazole (0.50mmol), Pd(PPh3)2Cl2 (0.025mmol, 5.0mol%), K2CO3 (1.0mmol, 2.0mol equivalent), DMF (2.0mL), distilled water (2.0mL) and the corresponding phenylboronic acid (0.60mmol), were added in a 10mL round bottom flask. The mixture was stirred at 90C for 24h. After completion of the reaction, the mixture was cooled down to room temperature and extracted 3 times with ethyl acetate. The combined ethyl acetate extract was dried using anhydrous MgSO4. The solvent was removed under reduced pressure and the product was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) followed by 7% methanol in ethyl acetate as an eluent.2.2.1 13 5-(4-Methoxyphenyl)-1-methyl-1H-imidazole (1) (0007) Yellow solid; isolated yield (83%); 1H NMR (500MHz, CDCl3) delta (ppm): 7.48 (s, 1H, C-H- arom), 7.30 (d, 2H, J=8.8Hz, C-H arom), 7.03 (s, 1H, C-H-arom), 6.96 (d, 2H, J=8.5Hz, C-H arom), 3.84 (s, 3H, CH3), 3.62 (s, 3H, CH3). 13C NMR (125MHz, CDCl3) delta (ppm): 32.20, 55.20, 114.03, 122.06, 127.39, 129.54, 129.78, 133.07, 138.47, 159.28 (C- arom); IR (v, cm-1): 3084, 2947, 1899, 1720, 1611, 1552,1491, 1234, 1116, 1023; GC-MS m/z: 188 (M+1). Anal. Calc. for C11H12N2O (188): C, 70.19; H, 6.43; N, 14.88. Found: C, 70.35; H, 6.83; N, 14.80.

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

Reference:
Article; Ibrahim, Mansur; Malik, Imran; Mansour, Waseem; Sharif, Muhammad; Fettouhi, Mohammed; El Ali, Bassam; Journal of Organometallic Chemistry; vol. 859; (2018); p. 44 – 51;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem