Category: 2302-25-2

Synthetic Route of 2302-25-2,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.

A mixture of 1-propanol (7.5 mL) and water (2.5 mL) was purged with nitrogen for 5 minutes. To the solution were added 4-bromo-1H-imidazole (146.97 mg, 1 mmol), 2-(hydroxyl-methyl)phenylboronic acid (190 mg, 1.25 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol), PPh3 (39.3 mg, 0.15 mmol) and potassium carbonate (276 mg, 2.0 mmol). After stirring at 85 C. for 16 h, the mixture was allowed to cool to room temperature and was partitioned between EtOAc (30 mL) and water (15 mL). The aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic layers were washed with water, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography on silica gel to afford the pure product (62 mg, 37% yield). 1H NMR: 4.48 (s, 2H), 6.25 (br s, 1H), 7.18-7.28 (m, 2H), 7.39-7.47 (m, 2H), 7.62 (d, 1H, J=7.0 Hz), 7.80 (d, 1H), 12.30 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-imidazole, its application will become more common.

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. Formula: C3H3BrN2

To a stirred solution of 4-bromo-1 /-/-imidazole (5.0 g; Aldrich Chemical Company,Inc., Milwaukee, Wl) in 100 ml_ anhydrous THF at -78C in an oven dried 500 ml_ 3 necked-round bottom flask was added t-butyl-lithium (48.0 ml_, 1.7 M in pentane) dropwise over 45 minutes with a dropping funnel. After complete addition, the mixture was warmed to about 100C to 15C for 2 hours and then it was cooled to -78C, and a cold (-780C) solution of diisopropyl disulfide (6.78 ml_) in 30 ml_ THF was added via cannula. The reaction was stirred for 16 hours allowing the bath to warm. The pale yellow solution was quenched with saturated NH4CI followed by neutralization with 10% HCI. The layers were separated and the aqueous extracted with THF three times. The combined organics were dried over MgSO4 and purified by flash chromatography (40+M, 100:0, 95:5, 90:10 ethyl acetate/methanol) to afford 3.3767 g of (l-6a); m/z 143.0 (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 2302-25-2, its application will become more common.

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, SDS of cas: 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%).LCMS (ESI) m/z 277 and 279 (M+H)+. Step 1: To a mixture of the regioisomers 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo,-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (643 mg, 2.3 mmol) from Step 1 of Example 32, acetamide(275 mg, 5.0 mmol), and Cs2CO3 (1.5 g, 5 mmol) in 1,4-dioxane (7 mL) was added N,N?-dimethylethylenediamine (500mL, 5 mmol). Argon was bubbled into the mixture for 5 min followed by the addition of CuI (221 mg, 1.1 mmol). Argonwas bubbled into the mixture for an additional 5 min. Then the reaction vessel was sealed and the mixture was heatedat 100 C for 15 h. The mixture was cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). TheEtOAc layer was separated, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc toafford a mixture of regioisomers N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)acetamide and N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)acetamide (170 mg, 29%) as an oil. LCMS (ESI) m/z 256 (M+H)+.

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; 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

Reference of 2302-25-2, These common heterocyclic compound, 2302-25-2, name is 4-Bromo-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.

General procedure: A reaction vessel A’-1 (1.74g, 17.0mmol), A’-2 (2.07g, 17.0mmol), Tetrakis(triphenylphosphine)palladium (0.7g, 1.08mmol), Potassium carbonate (5.3 g, 38.3mmol), toluene (60 mL), ethanol (20 mL) and distilled water (20 mL) were added, followed by stirring at 60 C for 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, dried over MgSO 4, and then the organic solvent was removed, and A-1 (1.67 g, 68%) was obtained by silica column method

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Choi Don-su; Choi Jin-sol; (70 pag.)KR2019/35043; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

To a solution of 4-bromo-1H-imidazole 1a (2 g, 13.70 mmol) in DMF (30 mL) was added 2,2-dimethyloxiraneIf (20 mL) and Cs2CO3 (8 g, 24.62 mmol). The mixture was stirred at 90 C overnight. Then the mixture was evaporatedto dryness. The residue was dissolved in DCM (30 mL), washed with water (10 mL*2) and brine (10 mL), dried overNa2SO4, filtered and concentrated to give the target compound 1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol 1b(2.7 g, pale yellow solid), yield: 90.6%.1H NMR(400 MHz, CDCl3) delta 7.33 (s, 1H), 6.94 (s, 1 H), 3.82 (s, 2H), 1.22 (s, 6H)

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; Medshine Discovery Inc.; Quingdao Huanghai Pharmaceutical Co., Ltd.; WU, Chengde; ZHANG, Zhiliu; YU, Tao; (125 pag.)EP3042907; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2302-25-2,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.

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%).LCMS (ESI) m/z 277 and 279 (M+H)+. Step 1: To a mixture of the regioisomers 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo,-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (643 mg, 2.3 mmol) from Step 1 of Example 32, acetamide(275 mg, 5.0 mmol), and Cs2CO3 (1.5 g, 5 mmol) in 1,4-dioxane (7 mL) was added N,N?-dimethylethylenediamine (500mL, 5 mmol). Argon was bubbled into the mixture for 5 min followed by the addition of CuI (221 mg, 1.1 mmol). Argonwas bubbled into the mixture for an additional 5 min. Then the reaction vessel was sealed and the mixture was heatedat 100 C for 15 h. The mixture was cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). TheEtOAc layer was separated, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc toafford a mixture of regioisomers N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)acetamide and N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)acetamide (170 mg, 29%) as an oil. LCMS (ESI) m/z 256 (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 4-Bromo-1H-imidazole, its application will become more common.

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

Reference of 2302-25-2,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.

A mixture of 4-bromopyridin-2-ol (0.49 g, 2.82 mmol), l-tetrahydropyran-2-yl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole (0.86 g, 3.10 mmol), granular K2CO3 (1.17 g, 8.47 mmol), PdCl2(dppf) (0.10 g, 0.14 mmol), l,4-dioxane (12 mL), and H20 (5 mL) was stirred at 80 C under an argon atmosphere overnight. The reaction mixture was diluted with brine (40 mL), and extracted with dichloromethane (2 x 60 mL). The extracts were combined, dried over anhydrous MgS04, filtered, and the filtrate was concentrated to dryness on a rotovap. The crude material was purified on a silica gel column (methanol in dichloromethane, 0-50%) to afford the desired 4-(l-tetrahydropyran-2-ylpyrazol-4-yl)pyridin-2-ol (0.56 g, 81%) as a white, fluffy powder. LC-MS 246.3 [M+H]+, RT 1.05 min.

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); 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. name: 4-Bromo-1H-imidazole

General Procedure 46 To a mixture of 4-bromo-imidazole (995 mg, 6.77 mmol), potassium hydroxide (380 mg, 6.77 mmol), potassium carbonate (936 mg, 6.77 mmol) and tetra-n-butyl ammonium bromide (109 mg, 0.339 mmol) in dichloromethane (7 mL) was added tert-butyl bromo acetate (0.50 mL, 3.4 mmol). After stirring overnight the reaction was filtered. The filtrate was dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, ethyl acetate to afford (4-Bromo-imidazol-1-yl)-acetic acid tert-butyl ester (696 mg, 79%).

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; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-1H-imidazole

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-lH-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 title compound (19 mg, 0.049 mmol, 35%). 1U NMR (DMSOd6) 12.11 (s, IH), 9.76 (s, IH), 8.59 (d, IH), 7.97 (d, 2H), 7.85 (td, IH), 7.70 (s, IH), 7.67 (s, IH), 7.56 (m, 2H), 7.36 (dd, IH), 7.21 (d, IH), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). MS (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:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); 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, SDS of cas: 2302-25-2

Step A. (Z -4-(3-(4-(4-Bromo- lH-imidazol- 1 -yl but-2-en- 1 -yr)-4,4-dimethyl-2,5- dioxoimidazolidin- 1 -yl)-2-(trifluoromethyl)benzonitrile. A mixture of (Z)-4-(3-(4-chlorobut-2-en-l-yl)-4,4-dimethyl-2,5-dioxoimidazolidin-l-yl)-2- (trifluoromethyl)benzonitrile (500 mg, 1.3 mmol), 4-bromo-lH-imidazole (191 mg, 1.3 mmol), and K2C03 (359 mg, 2.6 mmol) in DMF (5 mL) was stirred at room temperature for 5 hours. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL x 3). The extracts were combined, washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford (Z)-4-(3-(4-(4- bromo- 1 H-imidazol- 1 -yl)but-2-en- 1 -yl)-4,4-dimethyl-2,5-dioxoimidazolidin- 1 -yl)-2- (trifiuoromethyl)benzonitrile as a white solid (600 mg, 93%). LCMS (ESI) m/z: 496.1 [M+H]+.

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; BEAUFOUR-IPSEN (TIANJIN) PHARMACEUTICAL CO., LTD.; AUVIN, Serge; LANCO, Christophe; DUTRUEL, Oliver; CHAO, Qi; GU, Kaichun; WO2015/100617; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem