Category: 53484-15-4

Synthetic Route of 53484-15-4, These common heterocyclic compound, 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]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.

To a solution of 5-bromo-1-methyl-1H-benzo[dlimmdazole (1.0 g, 4.74 mmol) indioxane (10 mL) were added 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (1.5 g,5.68 mmol), sodium 2-ethylhexanoate (1.968 g, 11.86 mmol) and Pd(dppf)C12.DCM (247 mg,0.474 mmol) under N2. The mixture was stirred at 110 C for 4 h, poured into H20 (60 mL) andextracted with EA (50 mL x 2). The organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column chromatography (PE/EA = 1/1) to afford 1 -methyl-S -(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-benzo[d]imidazole (1.0 g, 82 %) as a yellow solid. LC-MS m/z: 259.1 [M+Hf?. tR= 1.67 min.

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C8H7BrN2

[000388j To a stirred solution of compound 1 (1.6 g, 1 eq) in aq. ammonia solution (5 mL), copper chloride (catalytic amount) was added and heated at 90 C in a sealed tube for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20% methanol in dichloromethane and filtered. The filtrate was evaporated under reduced pressure to afford the title compound 2. LCMS (mlz): 148.00 (M + 1).

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53484-15-4,Some common heterocyclic compound, 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, molecular formula is C8H7BrN2, 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.

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (S)-(4-(4-(tert-butoxycarbonyl)-3-methylpiperazine-l- carbonyl)-3-fluorophenyl)boronic acid (837 mg, 2.29 mmol, 1.00 equiv) in toluene (20 mL), 5-bromo-l-methyl- lH-l,3-benzodiazole (400 mg, 1.90 mmol, 0.83 equiv), Pd(PPh3)4 (264 mg, 0.23 mmol, 0.10 equiv), sodium carbonate(2M, 10 mL), ethanol (2.8 mL). The resulting mixture was stirred overnight at 95C. After cooled to room temperature, the resulting solution was diluted with 20 mL of H20, extracted with 3×30 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (90: 10). The collected fractions were combined and concentrated under vacuum. This resulted in 800 mg (77%) of the title compound as a brown solid. LC-MS (ES, m/z) 453 [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-benzo[d]Imidazole, its application will become more common.

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

53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H7BrN2

A mixture of 5-bromo-l-methyl-li7-benzo[7]imidazole (302.3 mg, 1.432 mmol), diphenylmethanimine (341.5 mg, 1.885 mmol), t-BuONa (271.1 mg, 2.821 mmol), BINAP (89.7 mg, 0.144 mmol) and Pd2(dba)3 (130.6 mg, 0.1426 mmol) in l,4-dioxane (10 mL) was heated to 100 C and stirred overnight under N2 atmosphere and then concentrated in vacuo. The residue was diluted with water (40 mL) and the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 50 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo to give the crude product as a brown solid (0.446 g), which was used directly in the next step without further purification.MS (ESI, pos.ion) m/z: 312.4 [M+H]+.

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H7BrN2

A microwave vial is charged with INTERMEDIATE J, 5-bromo-l-methyl- benzimidazole (12.1 mg, 0.0574 mmol), K3P04 (37.5 mg, 0.177 mmol), PdCl2(dppf)2 (3.6 mg, 0.0044 mmol), DMF (1 mL) and heated in the microwave for 15 minutes at 120C. The mixture is filtered on Millipore and concentrated to dryness. The residue is dissolved in MeOH (2 mL), treated with NaOMe (25% w/w, 10 0.044 mmol) and stirred overnight at room temperature. The mixture is then filter on SCX-2 SPE column, the column is wash with 2M NH3 in MeOH. The filtrate is concentrated to dryness and purified by reverse phase preparative HPLC to give the title compound (5.3 mg, 28%). XH NMR (400 MHz, Methanol-d4) delta 8.15 (s, 1H), 7.88 (m, 1H), 7.80 (m, 1H), 7.60 (m, 3H), 7.45 (m, 2H), 5.04 (d, J = 3.7 Hz, 1H), 4.50 (t, J = 3.5 Hz, 1H), 3.92 (s, 3H), 3.86 (m, 2H), 3.75 (t, J = 7.9 Hz, 1H), 3.65 (dd, J = 8.0, 3.1 Hz, 1H), 3.55 (m, 1H).

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Related Products of 53484-15-4,Some common heterocyclic compound, 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, molecular formula is C8H7BrN2, 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.

[000388j To a stirred solution of compound 1 (1.6 g, 1 eq) in aq. ammonia solution (5 mL), copper chloride (catalytic amount) was added and heated at 90 C in a sealed tube for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20% methanol in dichloromethane and filtered. The filtrate was evaporated under reduced pressure to afford the title compound 2. LCMS (mlz): 148.00 (M + 1).

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53484-15-4

To a solution of 5-bromo-1-methyl-1H-benzo[d]imidazole (200 mg, 0.33 mmol, 1 eq.) in 1,4-dioxane (10 mL) was added 5-(4,4,5,5-bis(pinacolato)diboron (287 mg, 1.13 mmol, 1.2 eq.), KOAc (276 mg, 2.82 mmol, 2 eq.), PdCl2(dppf).DCM (76 mg, 0.09 mmol, 0.09 eq.). The reaction mixture was deoxygenated with N2 and the reaction mixture was stirred at 80 C. for 16 h. The reaction was monitored by LCMS and found to be complete after 18 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with ethyl acetate (2*50 mL). Combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. Removal of solvent under reduced pressure gave crude which was purified by Combi-Flash (0-100% EtOAC-Hexane) to afford the desired product (120 mg, 49%) as brown oil.

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 53484-15-4.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (314 pag.)US2019/23702; (2019); 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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, A new synthetic method of this compound is introduced below., Product Details of 53484-15-4

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-(tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoic acid (2.35 g, 9.47 mmol, 1.00 equiv) in CH3CN/toluene (70/12 mL), 5-bromo- l-methyl- lH- benzo[d] imidazole (2 g, 9.48 mmol, 1.00 equiv), Pd(PPh3)4 (548 mg, 0.47 mmol, 0.05 equiv), sodium carbonate (0.4M, 50 mL, 2.00 equiv). The resulting solution was stirred for 18 h at 90C. After cooled to room temperature, the reaction mixture was poured into 50 ml of water. The mixture was washed with 2×100 mL of ethyl acetate and the aqueous layer was collected. The pH value of the solution was adjusted to 4 with hydrochloric acid (IN). The solids were collected by filtration and dried under vacuum. This resulted in 2 g (84%) of the title compound as a white solid, which was dried under vacuum. LC- MS (ES, m/z): 253 [M+H]+

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