Category: 1003-91-4

Adding a certain compound to certain chemical reactions, such as: 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, 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 1003-91-4, COA of Formula: C4H3Br3N2

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.

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, 2,4,5-Tribromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

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

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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1003-91-4

To a solution of Example 69b (84 g, 263.3 mmol) in dry THF (2L) was added EtMgBr (88 mL, 263.3 mmol, 3.0M in ether) slowly under N2.The reaction was stirred at r.t. for 2 hours. Then about 2.0L water was added and filtered concentrated and the residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69d (14.0 g) as white solid ‘HNMR (400 MHz, Chloroform- ) delta 7.48 (s, 1H), 3.63 (s, 3H). Example 69c (14.0g) as white solid. NMR (400 MHz, Chloroform- ) delta 6.94 (s, 1H), 3.60 (s, 3H). A solution of Example 69c&d (2.4 g, 10.0 mol) in ether (100 mL) was cooled to -78 C. under nitrogen atmosphere and then a 2.5 M n-BuLi solution in hexane (4.0 mL, 10.0 mol) added dropwise over 15 mins. The mixture was stirred at -78 C. for 30min and then DMF (2.0 mL) was added dropwise over 15 min. The mixture was stirred at -78 C. for 30min and quenched with saturated IN HQ (50 mL) at -78 C. The residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69e (1.8 g, yield 95%) as yellow solid. NMR (400 MHz, Chloroform-d) delta 9.77 (d, J = 0.9 Hz, 1H), 7.51 (s, 1H), 3.93 (s, 3H).

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 1003-91-4.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-91-4, 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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: [M(PPh3)4] (1.0 equiv.) was added as a solid to a toluene solution (15mL) of 1 or 2 (1.0 equiv.) in a Schlenk flask and was stirred overnight at room temperature. The solvent was removed under the vacuum. The resulted yellow residue was dissolved in DCM (2mL) and was precipitated by addition of n-pentane (15mL), filtered and dried in vacuum to afford the product as yellow powder.

The chemical industry reduces the impact on the environment during synthesis 2,4,5-Tribromo-1-methylimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Avinash, Iruthayaraj; Gupta, Vivek; Karthik, Vedhagiri; Anantharaman, Ganapathi; Journal of Organometallic Chemistry; vol. 851; (2017); p. 104 – 114;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-91-4, The chemical industry reduces the impact on the environment during synthesis 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

To a solution of Example 69b (84 g, 263.3 mmol) in dry THF (2L) was added EtMgBr (88 mL, 263.3 mmol, 3.0M in ether) slowly under N2.The reaction was stirred at r.t. for 2 hours. Then about 2.0L water was added and filtered concentrated and the residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 69d (14.0 g) as white solid ‘HNMR (400 MHz, Chloroform- ) delta 7.48 (s, 1H), 3.63 (s, 3H). Example 69c (14.0g) as white solid. NMR (400 MHz, Chloroform- ) delta 6.94 (s, 1H), 3.60 (s, 3H).

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, 2,4,5-Tribromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

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. 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H3Br3N2

2,4,5-tribromo-1-methyl-imidazole (1) (0.5g, 1.56mmol) and trimethyloxonium tetrafluoroborate (0.25g, 1.72mmol) in a Schlenk flask was charged with dichloromethane (30mL). The mixture was stirred overnight at room temperature to afford a colorless solid. The volatiles were removed in vacuum and the resulted solid was washed with diethyl ether (2¡Á15mL) and dried under vacuum to give 3 as colorless powder. Yield: 0.60g (91%). Mp: 304C. 1H NMR (DMSO-d6, 500MHz, delta, ppm): 3.78 (s, 6H, N-CH3). 13C NMR (DMSO-d6, 125MHz, delta, ppm): 38.1 (N-CH3), 112.0 (4,5-C-Br), 124.9 (C2-Br). IR (KBr, cm-1): 1637(m), 1554(m), 1504(s), 1445(m), 1396(m), 1329(m), 1295(m), 1056(vs), 1034(vs), 813(w), 641(w), 522(w). ESI MS: m/z 332.8081 [M-(BF4) ]+.

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:
Article; Avinash, Iruthayaraj; Gupta, Vivek; Karthik, Vedhagiri; Anantharaman, Ganapathi; Journal of Organometallic Chemistry; vol. 851; (2017); p. 104 – 114;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-91-4, These common heterocyclic compound, 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, 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 stirred suspension of NaH (68 mg, 1.71 mmol, 60% in mineral oil) in dry THF (5 mL) at 0 C was added a dry THF (6 mL) solution of 54 (268 mg, 1.14 mmol). After 30 min of stirring at 0 C, 2,4,5-tribromo-1-methyl-1H-imidazole [38] (399 mg, 1.10 mmol) was added. The reaction mixture was refluxed overnight, then cooled, and poured into ice water (?10 mL). The resulting mixture was extracted with EtOAc (2 * 10 mL). The combined organic phases were extracted with aq HCl solution (1M, 2 * 6 mL). The combined water phases were basified to pH 14 with a concentrated aq NaOH solution and extracted with EtOAc (3 * 10 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. Purification by DCVC (DCM:MeOH:NH3/100:0:0 to 100:13:1) gave 1-((4,5-dibromo-1-methyl-1H-imidazol-2-yl)oxy-N,N-dimethyl-7-phenylheptan-3-amine as a yellow oil (155 mg, 29%). 1H NMR (CD3OD, 400 MHz) delta 7.26-7.20 (m, 3H), 7.18-7.10 (m, 3H), 4.41-4.29 (m, 2H), 3.36 (s, 3H), 2.62 (t, 3H, J = 7.5 Hz), 2.33 (s, 6H), 2.00 (dq, 1H, J = 14.4, 7.8 Hz), 1.81 (dq, 1H, J = 7.8, 6.8 Hz), 1.69-1.61 (m, 4H), 1.39-1.37 (m, 2H). 13C NMR (CD3OD, 101 MHz) delta 129.55 (2C), 129.44 (2C), 126.85, 110.88, 69.83, 62.27, 40.79 (2C), 36.88, 32.82, 31.03, 30.32, 27.78.

Statistics shows that 2,4,5-Tribromo-1-methylimidazole is playing an increasingly important role. we look forward to future research findings about 1003-91-4.

Reference:
Article; Bach, Tinna B.; Jensen, Anders A.; Petersen, Jette G.; S¡ãrensen, Troels E.; Della Volpe, Serena; Liu, Jun; Blaazer, Antoni R.; Van Muijlwijk-Koezen, Jacqueline E.; Balle, Thomas; Fr¡ãlund, Bente; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 425 – 444;,
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