Category: 54624-57-6

Electric Literature of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Among them, “·” represents a boron hydrogen bond B-H. n-BuLi (1.6M) in n-hexane solution (1.00mL, 1.6mmol) was slowly added dropwise to the ortho-carboborane-o-C2B10H10 at -78 C(92.0 mg, 0.64 mmol) in tetrahydrofuran solution, stirring at this temperature for 30 minutes,After slowly increasing to room temperature, the reaction was continued for 1 hour and then bromobenzimidazole was added.(126.7 mg, 0.64 mmol), continued to react at room temperature for 6 hours. Then, the binuclear ruthenium compound [Cp*RhCl2] 2 (256.0 mg, 0.32 mmol) was added to the reaction system for further reaction for 3 hours.After completion of the reaction, the mixture was allowed to stand for filtration, and the solvent was evaporated to dryness, and the obtained crude product was subjected to column chromatography (petrole ether / THF / 6:1) to give a red target product (III).Complex Rh (265.6 mg, yield 78%).

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

Reference:
Patent; Shanghai Institute of Technology; Yao Zijian; Fan Xiaonan; Gao Yonghong; Deng Wei; (9 pag.)CN110117299; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) imidazo [1,2- a] pyridine(100 mg, 0.31 mmol),Palladium acetate (4 mg, 0.016 mmol),Triphenylphosphine (16 mg, 0.06 mmol),And sodium carbonate (66 mg, 0.62 mmol)After adding 1,4-dioxane and water at a ratio of 1: 1 in 2 mL portions2-Bromobenzimidazole (61 mg, 0.31 mmol) was added thereto, and the mixture was stirred at 90 ° C for 16 hours. After the reaction is completed, the reaction mixture is cooled to room temperature and the reaction product is separated into water and ethyl acetate. The extracted organic layers were concentrated and the concentrate was purified by silica gel column chromatography (dichloromethane: ethyl acetate, 10: 1 v / v) to give 2- (3- (imidazo [ ) Phenyl) -1H-benzimidazole (43 mg, 45percent).

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

Reference:
Patent; Korea Research Institute of Chemical Technology; Jeon Mun-guk; Kim Gwang-rok; Huh Yun-jeong; Lee Jun-mi; (27 pag.)KR2018/101671; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 54624-57-6, 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. 54624-57-6, name is 2-Bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of intermediate benzyl 2-bromo-1H-1,3-benzodiazole-1-carboxylate (7a) Under nitrogen atmosphere, benzyl chloroformate (0.174 mL, 1.218 mmol) was added to a solution of 2-bromo-1H-1,3-benzodiazole (200 mg, 1.015 mmol) and pyridine (0.123 mL, 1.523 mmol) in anhydrous dichloromethane (4 mL) at 0°C. The reaction mixture was stirred at room temperature for 3 hours, then cooled to 0°C. Water (5 mL) was added, and once at room temperature, the aqueous layer was extracted with dichloromethane (2 x 7 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate: 80/20) to provide benzyl 2-bromo-1H-1,3-benzodiazole-1-carboxylate (7a) (250 mg, 0.755 mmol, 74percent). 1H NMR (400 MHz, CDCl3) d 5.54 (s, 2H), 7.30-7.37 (m, 2H), 7.39-7.48 (m, 3H), 7.50-7.55 (m, 2H), 7.64-7.71 (m, 1 H), 7.85-7.92 (m, 1H).

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

Reference:
Patent; LABORATOIRE BIODIM; Ledoussal, Benoit; Le Strat, Frederic; Chasset, Sophie; EP2821104; (2015); 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. 54624-57-6, name is 2-Bromobenzimidazole, A new synthetic method of this compound is introduced below., name: 2-Bromobenzimidazole

(1) in 250mL three-necked flask,Purged with nitrogen,0.02mol raw material 2-bromo-1H-benzimidazole was added,0.03mol iodobenzene,0.04 mol sodium hydride, 0.004 mol copper iodideAnd 0.01 mol of o-phenanthroline were dissolved in 100 ml of 1,3-dimethyl-2-imidazolidinone,The reaction was stirred for 20-30h,After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and rinsed with a mixture of petroleum ether and ethyl acetate. The volume ratio of petroleum ether to ethyl acetate in the eluent was 1 : 100, purified by column chromatography to give Intermediate M1;HPLC purity 99.5%, yield 75.8%.

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Zhang Zhaochao; Tang Dandan; Li Chong; (40 pag.)CN106946853; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

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

Reference:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
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. 54624-57-6, name is 2-Bromobenzimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 54624-57-6

Tetrakis(triphenylphosphine)palladium(0) (0.028 g, 0.024 mmol) was added to a mixture of tert-butyl 4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoyl)piperazine-l- carboxylate (0.050 g, 0.120 mmol), 2-bromo-lH-benzo[d] imidazole (0.035 g, 0.180 mmol), and sodium carbonate (0.051 g, 0.480 mmol) in dioxane (1.5 mL) and water (0.30 mL). The mixture stirred in the microwave at 50°C for 3 h. The reaction mixture was filtered through Celite and concentrated. The residue was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 0-50percent ethyl acetate-hexane) to afford tert-butyl 4-(4-(lH-benzo[d]imidazol-2-yl)benzoyl)piperazine- 1-carboxylate (0.027 g, 0.066 mmol, 55 percent yield) as an off-white solid. MS (ESI, pos. ion) m/z: 407 (M + 1).

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; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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: To the corresponding benzimidazole or pyrazole 16?20 (4.5 or 6.6 equiv), dissolved under N2 atmosphere in anhyd MeCN, NaH (60percent dispersion in mineral oil, 4.5 or 6.6 equiv) was added and the mixture was stirred for 30 min at r.t. Then, the bromomethyl-substituted benzene derivative 15, 21 or 23 (1 equiv) was added and the reaction mixture was stirred for up to 5 d at r.t. under N2 atmosphere. The reaction was quenched with H2O (10 mL) and extracted with CHCl3 (3 × 10 mL). The organic layers were combined, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CHCl3?MeOH or CHCl3?MeOH?hexane as the eluent.

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

Reference:
Article; Koch, Niklas; Mazik, Monika; Synthesis; vol. 45; 24; (2013); p. 3341 – 3348;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 54624-57-6, These common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, 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.

To 2-bromo-1H-benzo[d]imidazole (0.75 g, 3.8 mmol) in THF (25 mL) was added n-butyllithium (1.5 mL, 3.8 mmol) dropwise at -78°C. After 45 minutes, a solution of racemic (1′-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-1′-yl-4-ium)trihydroborate (0.7 g, 4.6 mmol) from the reference example, in THF (15 mL) was added dropwise at -78°C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75°C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgSO4, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield racemic (3H-1′-azaspiro[benzo[4,5]imidazo[2,1-b]oxazole-2,3′-bicyclo[2.2.2]octan]-1′-yl-10-ium)trihydroborate (0.66 g, 2.5 mmol, 64.4 percent yield) as a white powder. 1H NMR (500MHz, DMSO-d6) d 7.44 – 7.34 (m, 1H), 7.31 – 7.19 (m, 1H), 7.18 – 6.97 (m, 2H), 4.53 (d, J=9.8 Hz, 1H), 4.31 (d, J=9.8 Hz, 1H), 3.45 (dd, J=15.3, 2.5 Hz, 1H), 3.36 – 3.29 (m, 1H), 3.09 – 3.01 (m, 1H), 2.99 – 2.83 (m, 3H), 2.43 (br. s., 1H), 2.15 – 2.04 (m, 1H), 1.92 – 1.75 (m, 3H), 1.69 – 1.20 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+1-BH3]+ = 256.12.

Statistics shows that 2-Bromobenzimidazole is playing an increasingly important role. we look forward to future research findings about 54624-57-6.

Adding a certain compound to certain chemical reactions, such as: 54624-57-6, name is 2-Bromobenzimidazole, 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 54624-57-6, name: 2-Bromobenzimidazole

To a stirred solution of Intermediate 13 (0.25 g, 0.92 mmol) in dry DMF (3 mL), TEA (0.5 mL, 3.71 mmol) and 2-bromo-1H-benzoimidazole (0.18 g, 0.92 mmol, Arbor chemicals) were added at rt and the reaction mixture was stirred at 100 °C overnight. It was cooled to rt and concentrated. This crude product was purified by flash column chromatography to afford the title compound (brown solid). 1H NMR (400 MHz, CDCl3): delta 7.33 (m, 2H), 7.07-7.06 (m, 2H), 6.86 (d, J=1.2 Hz, 1H), 6.76-6.74(m, 2H), 5.97-5.96 (m, 2H), 3.59-3.58 (m, 4H), 3.35-3.34 (m, 1H), 2.60-2.59 (m, 2H), 2.52-2.51 (m, 2H), 1.35 (d, J=8.0 Hz, 3H). LCMS: (Method A) 351.2 (M+H), Rt. 2.29min, 95.81 percent (Max). HPLC: (Method A) Rt. 2.19 min, 96.33percent (Max).

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Synthetic Route of 54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Sodium hydride (60% dispersion in mineral oil, 0.665 g, 16.63 mmol) was added to a solution of 2-bromo-lH-benzo[d]imidazole (2.73 g, 13.86 mmol) in DMF (30 mL), and the reaction stirred for 10 minutes at ambient temperature. l-Bromo-2-methoxy ethane (1.541 ml, 16.63 mmol) was added, and reaction stirred overnight at ambient temperature. The reaction was diluted with ethyl acetate and washed several times with brine. The organic layer was separated and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified via column chromatography on a 100 gram silica gel column eluting with 20-40%) ethyl acetate- hexane. The desired fractions were combined and concentrated to afford 2-bromo-l-(2- methoxyethyl)-lH-benzo[d]imidazole (2.9 g, 82%) as an orange oil. 1H NMR (300 MHz, DMSO-i) delta ppm 7.54 – 7.67 (m, 2 H) 7.14 – 7.34 (m, 2 H) 4.42 (t, j=5.28 Hz, 2 H) 3.67 (t, J=5.28 Hz, 2 H) 3.20 (s, 3 H).

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem