Month: July 2021

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. Computed Properties of C3H3BrN2

A mixture of 4-bromo-lH-imidazole (223 mg, 1.52 mmol), 4- fluorophenylboronic acid (425 mg, 3.03 mmol), copper (II) acetate (413 mg, 2. 28 mmol), pyridine (0.25 mL) and powdered 4A molecular sieves (1 g) in 1,2-dichloroethane (7mL) was stirred at room temperature under a slow stream of air for 44 hours. The reaction mixture was filtered through Celite (D, washing with ethyl acetate. The filtrate was concentrated and the residue purified by flash column chromatography on silica eluting with 10 to 20% ethyl acetate/isohexane to give the product as a white solid (135 mg, 37%). 8 (iH, 400MHz, CDCl8) 7.16-7. 22 (3H, m), 7.32-7. 37 (2H, m), 7.65 (1H, d, J = 1.5 Hz). MS (ES+) 241,243 ([MH]+).

The synthetic route of 4-Bromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93252; (2003); 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 71759-89-2 as follows. Recommanded Product: 5-Iodo-1H-imidazole

A mixture of 16 (150 mg, 0. 298 mmol), 4-IODOIMIDAZOLE (86.7 mg, 0.447 mmol), dichlorobis (triphenylphosphine) palladium (II) (20.9 mg, 0.0298 mmol), LiCl (37.9 mg, 0. 894 MMOL) 9 M AQ. NA2CO3 (0.75 mL, 0.75 mmol) in toluene (1.8 ML) and EtOH (1. 8 ML) was microwaved at 120 C for 15 min. The reaction mixture was cooled, brine (3 mL) was added and the aqueous layer extracted with ethyl acetate (3 X 5 ML). Sorbent (HM-N, Jones Chromatography) was added, the solvent evaporated and the product purified by silicagel chromatography using MEOH : CH2CL2 (3: 97) (gradient elution) to give product 17 as A brown foam (111 mg, 84%); 1H NMR (400 MHz, CDCl3) 62. 96 (s, 6H), 6.77 (d, J = 8. 8 Hz, 2H), 7.48-7. 35 (m, 5H), 7.52 (t, J = 7. 6 Hz, 1H), 7.81 (s, 1H), 7.99 (s, 1H), 8. 11 (d, J = 7.5 Hz, 2H), 8. 27 (d, J = 2.0 Hz, 1H), 8.61 (d, J = 2. 1 HZ, 1H).

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2004/78756; (2004); A2;,
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. 3034-62-6, name is 2-Iodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-1H-imidazole

The organic material was extracted with ethyl ether, washed with 10% aqueous NaS2 O3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=3:2) to give the title compound as a light yellow oil (639 mg, 37%) and the corresponding 2-iodoimidazole as a light yellow solid (245 mg, 14%). PNMR (CDCl3, 300 MHz): d 2.89 (s, 6H) 7.34 (s, 1H), 7.78 (s, 1H).

According to the analysis of related databases, 3034-62-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US5475113; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 19225-92-4,Some common heterocyclic compound, 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, molecular formula is C5H7ClN2, 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 solution of tert-butyl 5-(2-(3-hydroxyphenyl)quina7.olin-4-ylamino)- l H- indazole-1-carboxylate (50mg, 0. 1 1 mmol), 2-(chloromethyl)-l -methyl- 1 H-imidazole (22 mg, 0.13 mmol), KI ( 22 mg, 0. 13 mmol), K2CO3 (76 mg, 0.55 mmol) in anhydrous DMF (1.2 niL) was heated at 50″C for 100 minutes. Added 1.2 equivalents each of 2- (chloromethyl)-l -methyl- l H-imidazole and Kl and heated for another 35 minutes. Added 2.4 equivalents each of 2-(chloromethyl)- l -methyl-l H-imidazole and Kl along with 2.0 equivalents of K2COj and heated for 1 h. The solution was diluted with CH2Cl2 and washed with aqueous saturated NaCI (2x). The organic phase was dried under Na2SO.) and concentrated /’// vacuo to afford tert-butyl 5-(2-(3-(( l -methyl- 1 H-imida7.ol-2-yl)methoxy)- phenyl)quinazolin-4-ylamino)- 1 H-indazole- 1 -carboxylate.

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

Reference:
Patent; SURFACE LOGIX, INC.; SWEETNAM, Paul; BARTOLOZZI, Alessandra; CAMPBELL, Anthony; COLE, Bridget; FOUDOULAKIS, Hope; KIRK, Brian; SESHADRI, Hemalatha; RAM, Siya; WO2010/104851; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 20485-43-2, The chemical industry reduces the impact on the environment during synthesis 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

HATU (O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate) (1.75g; 4.60 mmol) was added in on portion to a stirring solution of 1-methyl-1 H- imidazole-2-carboxylic acid (509 mg; 4.04 mmol), lambda/,O-dimethylhydroxylamine hydrochloride (391 mg; 4.01 mmol), and diisopropylethylamine (2.0 ml 1 1.9 mmol) in anhydrous DMF (14 ml_). The mixture was stirred at room temperature for 17 hours and partitioned between ethyl acetate (100 ml.) and water (100 ml_). The organic phase was dried (MgSO4) and concentrated in vacuo, giving a colourless oil (1.45 g). This was purified by column chromatography, giving the title compound as a colourless oil (494 mg; 73%). 1H-NMR (400MHz, CDCI3): 3.57 (3H, br s), 3.86 (3H, s), 3.91 (3H, s), 6.97 (1 H, d, J=I Hz), 7.07 (1 H, d, J=I Hz).

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, 1-Methyl-1H-imidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107539; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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. name: 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

Example 16a) 7,00 g (24.7 mmol) 1-bromo-4-iodo-benzene, 10.5 g (32.2 mmol) caesium carbonate, 2.36 g (12.4 mmol) copper(l) iodide and 2.85 g (24.7 mmol) L-proline are added to 5.13 g (24.7 mmol) mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 80 ml DMSO under nitrogen. The reaction mixture is stirred for 15 h at 100 C and 4 h at 150 C, filtered on Hyflo with dichloromethane. The organic phase is washed with water. The organic phase is dried with magnesium sulfate. The product is decocted with diethylether and methyl ethyl ketone (MEK). Yield: 2.90 g (77 %).1H NMR (400 MHz, DMF-d7): delta 7.93-8.10 (m, 4H), 7.78-7.92 (m, 2H), 7.72-7.79 (m, 1 H),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28890-99-5, its application will become more common.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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. Computed Properties of C7H7N3

General procedure: A mixture of 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol), arylaldehyde (1.0 mmol), dimedone (1.0 mmol), and 15 mol % p-TsOH.H2O was stirred in 5 cm3 acetonitrile as solvent at 40-50 C for the appropriate time (Table 3). The progress of the reaction was monitored by TLC. After completion of the reaction, a thick precipitate was obtained. The solid product was filtered off and washed with acetonitrile and subsequently dried in air. The pure product was characterized by conventional spectroscopic methods.

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Monatshefte fur Chemie; vol. 145; 12; (2014); p. 1967 – 1973;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H5BrN2

Intermediate 3: Step b (1-Methyl-1H-imidazol-5-yl)(thiazol-5-yl)methanone To a solution of 5-bromo-1-methyl-1H-imidazole (1.14 g, 7.11 mmol) in DCM was added ethyl magnesium bromide (2.34 mL, 7.11 mmol; 3 M in diethyl ether) dropwise over a 10 minute period. The resulting pale yellow solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methylthiazole-5-carboxamide (Intermediate 3, step a) (1.02 g, 5.92 mmol) dissolved in DCM (3 mL) was added dropwise. The cold bath was removed and the reaction mixture stirred at room temperature for 48 hours. To the resulting yellow suspension was added water followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitates were collected by filtration and dried to provide the title compound as a tan solid.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; US2014/107096; (2014); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 33543-78-1

An ice-cold solution of ethylimidazole-2-carboxylate (5.1 g, 36.4 mmol) in conc sulfuric acid (15 mL,281 mmol) was treated dropwise with fuming HNO3 (15 mL). The mixture was heated at 60 °C for 2.5 hr, cooled and then poured onto ice (150 g). The resulting solid was collected by vacuum filtration, washed with water, and dried in vacuo to afford the title compound 12p as a colourless powder (4.2 g, 64percent). LCMS: Rt = 2.49 min, 99 Apercent 254 nm, [M – H]- = 184.0. 1H NMR (600 MHz,DMSO-d6) delta 8.55 (s, 1H), 4.38 (q, J = 7.1 Hz, 2H), 1.35 (t, J = 7.1 Hz, 3H). 13C NMR (150 MHz,DMSO-d6) delta 157.6, 147.4, 135.9, 122.1, 61.9, 14.0. The 1H data was consistent with previousreports [4].

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, molecular formula is C5H8N2O, 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. Recommanded Product: 38993-84-9

A mixture of (1-methyl-1H-imidazol-5-yl) methanol (500MG, 4.5 mmol) in DMF (5 ML) at-5 oC was slowly treated with thionyl chloride (0.49 ML, 6.7 mmol), stirred an additional 10 minutes AT-5 C, warmed to room temperature, stirred 1.5 hours, cooled TO-5 C, quenched with isopropyl alcohol and ethyl acetate, stirred 30 minutes AT-5 C, concentrated under vacuum, and filtered to collect the solid. The solid was rinsed with ethyl acetate and dried under vacuum to give (212mg, 28percent) of the desired product as the hydrochloride salt. MS (DCI) m/e 131 (M+H) + ; 1H NMR (300 MHz, DMSO-D6) 8 9.10 (S, 1H), 7.76 (s, 1H), 5.02 (s, 2H), 3.88 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38993-84-9, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem