Category: 2302-25-2

Electric Literature of 2302-25-2, The chemical industry reduces the impact on the environment during synthesis 2302-25-2, name is 4-Bromo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-bromo-1H-imidazole (2.59 g, 17.6 mmol, Eq: 1.00) and di-tert-butyl dicarbonate (4.04 g, 4.3 ml, 18.5 mmol, Eq: 1.05) were combined with tetrahydrofuran (19 ml). Dimethylaminopyridine(43.1 mg, 352 imol, Eq: 0.02) was added and the reaction was stuffed at 25C for 1.5 h. Thecrude reaction mixture was concentrated in vacuo. The residue was taken up in ethyl acetate and washed with a solution 1M of hydrogen chloride, water, saturated sodium bicarbonate and brine. The organic layer was dried and concentrated in vacuo to afford the desired compound as an off- white solid (4.2 g, 95%).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2, name: 4-Bromo-1H-imidazole

General procedure: Amberlyst A21 (20 wt %) was added to a mixture of amine (1 mmole) and (Boc)2O (1 mmole) and the mixture was stirred for the appropriate reaction time as specified in (Table 1). The progress of reaction was monitored by Thin layer chromatography (10-20% ethyl acetate: hexane) on TLC plates (Merck) precoated with silica. After completion of reaction, the reaction mass was diluted with methanol, filtered off the catalyst which was washed for several times and then dried at 800 C under reduced pressure for 1 hour and subjected to further recycle study (Table 4). It showed no much more decrease in the product yield indicating high activity of the catalyst. The filtrate was concentrated on rotavacc and the product was purified by column chromatography to afford pure products.

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:
Article; Tekale, Sunil U.; Kauthale, Sushama S.; Pawar, Rajendra P.; Journal of the Chilean Chemical Society; vol. 58; 1; (2013); p. 1619 – 1623;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A dried pressure tube was charged with 4-bromo-1H-imidazole (100 mg, 667 mumol), tetrahydrofuran (3 ml), N,N-dimethylformamide (2 ml), 2-(methylsulfonyl)-5-(trifluoromethyl)pyridine (150 mg, 667 mumol), and cesium carbonate (261 mg, 800 mumol). The tube was sealed and heated at 105 C. for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 60:30 as the eluent. The 2-(4-bromo-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine (167 mg, 86% yield) was obtained as a crystalline white solid. MS (ISP): m/z=292.0 [M+H]+ and 294.2 [M+2+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, 4-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Narquizian, Robert; Woltering, Thomas; Wostl, Wolfgang; US2012/253035; (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 2302-25-2 as follows. 2302-25-2

To a solution of 4-bromo-7H-imidazole (lg, 6.80 mmol) in DMF (20 ml) was added NaH (0.272 g, 6.80 mmol) at 0 C. The mixture was stirred for 10 minutes, tert-butyl (3- bromopropyl)carbamate (1.62 g, 6.80 mmol) was added. The solution was stirred at room temperature for 2 hours and then heated at 50C for 1 hour. The mixture was quenched with water (50 ml) and extracted with EtOAc (3×20 ml). The organic layer was washed with water (30mL), brine (30mL) and dried over Na2SC”4. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (Redi 40g gold column), and eluted with EtOAc/Hexane (0-100%, 6cv; 100%, lOcv) to give the title compound. LC-MS [M + H]+: m/z 304.19. 1HNMR (500 MHz, CDC13) delta 7.40 (s, 1 H); 6.94 (s, 1 H); 4.67 (s, 1 H); 3.98 (t, J = 7.0 Hz, 2 H); 3.17 (d, J = 7.5 Hz, 2 H); 1.98 (p, J = 6.8 Hz, 2 H); 1.47 (s, 9 H).

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; LIU, Weiguo; DING, Fa-Xiang; SUN, Wanying; ZANG, Yi; PAN, Weidong; OGAWA, Anthony; BROCKUNIER, Linda; HUANG, Xianhai; WANG, Hongwu; MAL, Rudrajit; BIFTU, Tesfaye; PARK, Min; GUO, Yan; JIANG, Jinlong; CHEN, Helen; PLUMMER, Christopher, W.; (258 pag.)WO2017/106064; (2017); 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 2302-25-2 as follows. 2302-25-2

Step 1: To a stirred mixture of DMF (15 mL) and NaH (60% dispersion in mineral oil, 539 mg, 21 mmol) at 0C under argon was added 4-bromo-1H-imidazole (3 g, 20 mmol) in one portion. The mixture was stirred for 5 min at 0C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.3 mL, 24 mmol) in DMF (3 mL) was added dropwise. Afterstirring at 0 C for 1 h, the mixture was warmed slowly to rt and stirred for 6 h. The mixture was then partitioned betweenEtOAc (100 mL) and water (50 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4, filtered,and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography(eluting with a gradient of 100% hexanes to 100% EtOAc) to afford a regioisomeric mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as an oil (2.9 g, 53%). Step 2: To a mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (345 mg, 1.3 mmol) from Step 1 of this Example, and 1-methylpyrazole-4-boronicacid pinacol ester (390 mg, 1.9 mmol) in DME (3 mL) was added K2CO3 (691, 5 mmol). Argon was bubbled into themixture for 5 min followed by the addition of Pd(PPh3)2Cl2 (44 mg, 0.06 mmol). Argon was bubbled into the mixture foran additional 5 min. Then the reaction vessel was sealed and the mixture was heated at 100 C for 15 h. The mixturewas cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). The EtOAc layer was separated andwashed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified viasilica gel flash chromatography eluting with a gradient of 100% CH2Cl2 to 10% MeOH in CH2Cl2 to afford a regioisomericmixture of 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-1H-pyrazole and 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-1H-pyrazole as an oil (280 mg, 82%). LCMS (ESI) m/z 280 (M+H)+. Step 3: A mixture of 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-1-pyrazole and 1-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)-1H-pyrazole (170 mg, 0.7 mmol) from Step 2 of this Examplewere stirred in a 1:1 mixture of TFA and CH2Cl2 (5 mL) for 15 h. The mixture was then concentrated under reducedpressure to afford 4-(1H-imidazol-4-yl)-1-methyl-1H-pyrazole (248 mg) as an oil and was used in the next step withoutfurther purification. LCMS (ESI) m/z 149 (M+H)+.

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below.

General procedure: The corresponding imidazole (2 mmol) and 2-bromoethanol or 3-bromo-1-propanol or 4-bromo-1-butanol (2.4 mmol) dissolved in acetone (20 ml). Then K2CO3(6 mmol) and KI (2 mmol) were added. The reaction mixture was stirred at 60oCfor 12h. Filtered, the filtrate was concentrated under reduced pressure and dried under vacuum. The1H-NMR and13C-NMR were consistent with the literature.

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:
Article; Hu, Yanping; Li, Na; Zhang, Jiayao; Wang, Ying; Chen, Li; Sun, Jianbo; Bioorganic and Medicinal Chemistry Letters; vol. 29; 9; (2019); p. 1138 – 1142;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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. 2302-25-2

Step 3: 4-Bromo-1 H-imidazole (Aldrich) (500 mg, 3.40 mmol) is charged in a round-bottom flask and dissolved in THF (10 ml_). 2-Bromoacetophenone (Aldrich) (1 .35 g, 6.80 mmol, 2.00 eq) and potassium carbonate (940 mg, 6.80 mmol, 2.00 eq) are added. The reaction mixture is stirred for 16 h at RT, diluted with EtOAc and washed with water. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (100 % hexanes to 50 % EtOAc in hexanes) to provide intermediate 4044C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2302-25-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2.

Add tetrakis (triphenylphosphine) palladium (0) (500 mg) to a degassed suspension of H-IMIDAZOLE (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4- (2- ISOPROPOXYPHENYL)-1H-IMIDAZOLE (5.01 g, 73%) which is used without further purification in the next step.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2.

The 2-(4-bromo-lH-imidazol-l-yl)-5-(trifluoromethyl)pyridine was obtained as follows:A dried pressure tube was charged with 4-bromo-lH-imidazole (100 mg, 667 muiotaetaomicron), tetrahydrofuran (3 ml), N,N-dimethylformamide (2 ml), 2-(methylsulfonyl)-5- (trifluoromethyl)pyridine (150 mg, 667 muiotaetaomicron), and cesium carbonate (261 mg, 800 muiotaetaomicron). The tube was sealed and heated at 105 C for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate = 100:0 to 60:30 as the eluent. The 2-(4-bromo-lH- imidazol-l-yl)-5-(trifluoromethyl)pyridine (167 mg, 86% yield) was obtained as a crystalline white solid. MS (ISP): m/z = 292.0 [M+H]+ and 294.2 [M+2+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, 4-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A.; NARQUIZIAN, Robert; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/136603; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2302-25-2 name is 4-Bromo-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. 2302-25-2

1 (300 mg, 2.05 mmol), DCM (10 mL), TEA (3.0 eq), (Boc)20 (1.2 eq), 0C for 10 min; gradually warmed to RT for 10 min and stirred. After 16 h, a non-polar product was observed by TLC. The reaction was quenched with water and extracted with EtOAc (2X20 mL). The combined organic layer was washed with water and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the crude which was purified by silica gel column chromatography [using 100-200 mesh, eluting with 20% EtOAc-hexane] to afford 320 mg of 2 as white solid. Repeat preparation with 1 (1 g, 6.83 mmol), DCM (20 mL), TEA (3.0 eq), (Boc)20 (1.2 eq), 0 oC-RT. After 16 h, one non-polar product was observed by TLC. The reaction mixture was quenched with water and extracted with EtOAc (2X30 mL). The combined organic layer was washed with water and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the crude which was purified by silica gel column chromatography [using 100-200 mesh, eluting with 20% EtOAc-hexane] to afford 1.2 g of 2 as white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; UNITHER VIROLOGY, LLC; RAMSTEDT, Urban; WARFIELD, Kelly Lyn; TRESTON, Anthony; (147 pag.)WO2016/73652; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem