Tag: M.W=300-400

2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

Example 1.1.3bis(pinacolate)diborane81%[0044] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-lH- benzo[d]imidazole (3): A mixture of Compound 2 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533g, 2.1 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Ci2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (KOAc) (0.393 g, 4mmol) in 1,4-dioxane (20 ml) was heated at 80 C under argon overnight. After cooling to RT, the whole was diluted with ethyl acetate (80 ml) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid 3 (0.64 g, in 81% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, its application will become more common.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; MA, Liping; MOCHIZUKI, Amane; LAI, Qianxi; KHAN, Sazzadur, Rahman; LI, Sheng; HARDING, Brett, T.; CHAE, Hyunsik; ROMERO, Rebecca; SISK, David, T.; WO2012/88294; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 33016-47-6

[1816] To a stirred solution of starting material benzyl amine (0.99 g, 8.87 mmol) in MeOH (50 mL) under nitrogen inlet at room temperature, was added sodium acetate (0.73 g, 8.87 mmol), 3A molecular sieves (3.0 g) and aldehyde (3.0 g, 8.87 mmol). The resulting solution was stirred at room temperature overnight, followed by addition of NaBH4 (0.67 g, 17.74 mmol), then stirred for 4 hrs and concentrated to dryness, followed by extraction with CH2Cl2-1N NaOH. The combined organic layer was dried over MgSO4, filtered, concentrated to dryness and purified by column chromatography on silica gel, eluting with 2%MeOH-NH3/98%CH2Cl2 to give light yellow oil (3.75 g, 98% yield, MH+=430.2)

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, 33016-47-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhu, Hugh Y.; Njoroge, F. George; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Vibulbhan, Bancha; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.; US2003/229099; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 152628-02-9, 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.

10 g (0.0329 mol) of 2-propyl-4-methyl-6-(r-methylbenzimidazole-2- yl)benzimidazole (1) was dissolved in 60 ml of dimethylsulfoxide (DMSO). 3.7 g (0.0329 mol) of Potassium tert-butoxide was added to the aforementioned solution and stirred at room temperature (25-3O0C) for 30 min. Afterwards, 11.45 g (0.0329 mol) of tert-Butyl-4-bromomethylbiphenyl-2-carboxylate (2) was added and the obtained mixture was stirred at room temperature (25-3O0C) for 3 h. At this stage, the reaction was quenched with water (400 ml) and stirred for 30 min. The reaction mass was filtered. The resulting wet cake was slurried in water (200 ml) and stirred for 30 min. The reaction mass was filtered and the obtained solid was dried under vacuum at 60-650C until constant weight. 18.3 g obtained (93% HPLC).

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Patent; INKE, S.A.; SINGH, Santosh; JOSHI, Anil; NEWADKAR, Ravindranath; WO2010/149565; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, A common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.

In a 500 mL four-necked flask equipped with a mechanical stirrer and a thermometer, 30.0 g (98.6 mmol) of 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole, 124 g of methylpyrrolidone and 11.1 g (98.9 mmol) of potassium tert-butoxide were added and stirring was started. While cooling the 4-necked flask with ice water, a solution of 33.1 g (108.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid methyl ester in 124 g of N-methylpyrrolidone was heated at an internal temperatureWas added dropwise at 0 to 10 C. over 25 minutes.After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 3 hours.The reaction solution was sampled and analyzed by HPLC. As a result, 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole was not detected and 82.5%4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- there were.150 g of water and 130 g of toluene were placed in a 1000 mL four-necked flask equipped with a mechanical stirrer, and while stirring,A reaction solution of a 500 mL four-necked flask was added dropwise.30 g of 35% hydrochloric acid was added to acidify the aqueous layer, and the organic layer and the aqueous layer were separated.209 g of toluene and 46 g of 25% sodium hydroxide aqueous solution were added to the aqueous layer,The aqueous layer was made alkaline and separated into an organic layer and an aqueous layer.An aqueous layer and 78 g of toluene were put into a 500 mL separating funnel and extracted,It was separated into an organic layer and an aqueous layer.The organic layers were combined and concentrated,A solution of 4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2- propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- 63.3 g of crude product was obtained. This crude product contained about 13.5 g of toluene, and the content of the target product was 49.8 g (yield 95.6%).

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
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. 1003-91-4 name is 2,4,5-Tribromo-1-methylimidazole, 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. 1003-91-4

To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) at room temperature was added bromine (9.6 g, 60.07 mmol) dropwise as a solution in 20 mL acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo, the residue was suspended in 500 mL water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give 2,4,5-tribromo-l-methyl- lH-imidazole (1.82 g, 29% – some product remained in the mother liquor) as a light yellow powder. Used without further characterization. To a suspension of the tribromide (1.82 g, 5.71 mmol) in 45 mL water was added sodium sulfite (13 g, 103 mmol) and the resulting mixture was stirred at rapid reflux for 24 h. After cooling to room temperature, organics were extracted with ether (3 chi 75 mL), dried over magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tri-, di- and monobromoimidazoles. This mixture was re-subjected to the reduction conditions (same quantity of sodium sulfite) using 15 mL of 3: 1 water/acetic acid as solvent and heating in a sealed vessel at 130 C for 60 h. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 by addition of 2 N sodium hydroxide. Organics were extracted with ether (3 chi 50 mL), dried over magnesium sulfate, filtered and concentrated to give crude 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 62%). Used without further characterization.. 4-Butyl-l -methyl- lH-imidazole (95 mg, 22 %) was synthesized as in Example 3.1 using 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 3.53 mmol) in place of 5-bromo-2- formylfuran and propylboronic acid (372 mg, 4.24 mmol) in place of hexylboronic acid. Used without further characterization. To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at – 0C was added -butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to -20 C over 20 minutes. After cooling to -78 C, 4-butyl-l -methyl- lH-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at -78 C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3 chi 20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give l -methyl-4-propyl-lH-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Tribromo-1-methylimidazole, and friends who are interested can also refer to it.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; PROVID PHARMACEUTICALS INC.; EBRIGHT, Richard H.; EBRIGHT, Yon W.; SHEN, Juan; BACCI, James; HIEBEL, Anne-Cecile; SOLVIBILE, William; SELF, Christopher; OLSON, Gary; WO2013/192352; (2013); 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 15469-97-3 as follows. 15469-97-3

(i) (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol In an argon atmosphere, n-butyllithium (1.6 M solution in hexane, 6.9 ml) was added drop by drop to a solution of 1-tritylimidazole (3.10 g) in THF (80 mL) under ice cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 mL) was added. After stirring under ice cooling for 1.5 hours and at room temperature for 1 hour, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saline and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1) to yield the titled compound (1.402 g) as a pale-yellow oily substance. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J=2.8 Hz, 18.0 Hz), 3.08 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.21 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J=1.4 Hz), 6.93 (1H, d, J=1.4 Hz), 7.0-7.4 (20H, m).

According to the analysis of related databases, 15469-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Naito, Kenichiro; Furuya, Shuichi; Tasaka, Akihiro; Ban, Toshikazu; US2004/138160; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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 152628-02-9.

Example 3 Preparation of f4′ – [2-n-propyl-4-methyl-6-(1-methyl benzimidazol-2-vl) benzimidazol -1-vl methvll biphenvl-2-carboxvlic acidl 50 gm of [1 H – Benzimidazole-2-n – propyl-4-methyl-6-(1′-methyl benzimidazole-2′- yl) ] was added to 200 ml dimethyl sulfoxide and 50 gm of sodium hydroxide. To this was added 60 gm of methyl-4- (bromomethyl) biphenyl-2-carboxylate at ambient temperature. The contents were stirred for 2 hours at 25-30 C and then heated to 40-50 and maintained for 2 hours. About 500 ml water was added to the reaction mixture and acidified with acetic acid to pH 4.2, extract4ed twice with 250 ml of dichloromethane and the combined extracts were concentrated and isolated by filtration after addition of 300 ml acetone, dried under reduced pressure at 50-60 C to give 75.0 gm (80%) of the title compound.

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIPLA LIMITED; TURNER, Craig, Robert; WO2005/108375; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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. 152628-02-9

In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2′- cyanobiphenyl was added. The reaction mass was warmed to 80 C and maintained for 4 hours at 80 to 85 C. The completion of the reaction was monitored by TLC using mobile phase chloroform : methanol (9:1). After completion of the reaction, the mass was cooled to 20 C, maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4′-(2″-n-propyl-4″-methyl- 6″-(r”-methylbenzimidazol-2″‘-yl)benzimidazol-l”- ylmethyl) biphenyl, melting at 196 – 198 C. C 80.53%, H 5.70%, N 14.20%; m/z = 496.64 1H NMR DMSO d6 400 Mhz : 5ppm 0.96 – 0.99 (t, 3H) 1.75 – 1.84 (m, 2H) 2.62 (s, 3H) 2.89 – 2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18 – 7.92 (m, 14H)

Statistics shows that 152628-02-9 is playing an increasingly important role. we look forward to future research findings about 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5’-bibenzo[d]imidazole.

Reference:
Patent; U AMARNATH, Amarnath; U SURYAKIRAN, Suryakiran; WO2014/27280; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15813-09-9, Adding a certain compound to certain chemical reactions, such as: 15813-09-9, name is 4,5-Diiodo-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 15813-09-9.

Preparation 71 4-iodo-1H-imidazole To a solution of 4,5-diiodo-1H-imidazole (Preparation 70, 7.7 g, 24 mmol) in ethanol (80 ml) and water (20 ml) was added solid sodium sulfite heptahydrate (20 g, 79 mmol). The reaction mixture was heated at reflux for 16 h, cooled, and the solid by-products were removed by filtration. The filtrate was then concentrated in vacuo and the resultant solid was dnred by suction. The crude residue was recrvstallised from dichloromethane to give the title compound as a white solid (4.6 g, 64%). NMR (CDCl3, selected data for the free base: 7.0 (s 1H), 7.5 (s, 1H). MS (TSP): M/Z (MH+): 195.2; C3H3129IN2+H requires 194.9.

According to the analysis of related databases, 15813-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer INC; US6313312; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 152628-02-9, 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.

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem