Imidazoles-derivatives

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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole

2-Chloro-1H-benzimidazole (7.5 g, 49 mmol) was dissolved in dimethylformamide (20 mL),and the reaction mixture was cooled to oo C. Sodium hydride ( 60% dispersion in mineral oil 2.16 g,5 5.4 mmol) was carefully added. The reaction mixture was stirred at ambient temperature for 1 hour,and after that iodomethane (8.37g, 59 mmol) was added. The reaction mixture was stirred at ambienttemperature overnight, and then water (200 mL) was added. The solid was collected by filtration toafford 5 g, 61% of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 3.79(s, 3H), 7.21-7.33 (m, 2H), 7.58 (t, J=7.0 Hz, 2H).

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); 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. 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(2-Bromophenyl)-1H-imidazole

Example 20 2-[2-({4-[(2,4-difluorophenoxy)methyl]phenyl}sulfonyl)plienyl]-l/r-imidazole; 2-(2-Bromophenyl)-lH-imidazole (WO 9407486; 1.0 g, 4.48 mmol) was dissolved in TEtaF (11 mL) and DMF (11 mL) and cooled to 00C. Sodium hydride (60percent dispersion in mineral oil, 197 mg, 4.93 mmol) was added and the reaction stirred for 20 min. 2-(Trimethylsilyl)ethoxymethyl chloride (0.79 mL, 4.93 mmol) was added and the reaction stirred overnight at room temperature. The reaction was quenched with MeOH then partitioned between water and Et2O. The organic layer was dried over MgSO4 and EPO concentrated in vacuo. The residue was purified by flash column chromatography, then used according to the method of Example 15 Step 1, followed by SEM-deprotection using trifluoroacetic acid in dichloromethane, to give the title compound. 1H NMR (500 MHz, DMSO): delta 12.10 (1 H, s), 8.24 (1 H, d, J 6.9 Hz), 7.77-7.71 (2 H, m), 7.65 (2 H, d, J 8.0 Hz), 7.53-7.50 (3 H, m), 7.29 (1 H, t, J 8.6 Hz), 7.23- 7.18 (2 H, m), 6.99 (1 H, t, J 7.6 Hz), 6.90 (1 H, s), 5.20 (2 H, s); m/z (ES+) 427 [MH+].

According to the analysis of related databases, 162356-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2006/97766; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 37067-95-1,Some common heterocyclic compound, 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

HL3: 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (1.0 mmol), Pd(OAc)2 (0.05 equiv), PPh3 (0.2 equiv), 1-methyl-2-iodoimidazole (2.5 mmol) were resolved in dimethoxyethane/2M K2CO3 aqueous solution (20 mL, 1:1) under nitrogen atmosphere. The mixture was heated and refluxed for 24 h. After being cooled to room temperature, the reaction mixture was diluted with EtOAc, and poured into a brine solution. The organic layer was separated, and washed with the water, dried, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the pure product HL3 in 34% yield. 1H NMR (CDCl3): 3.72 (s 6H), 7.12 (d, 2H), 7.47 (t, 1H), 7.48 (d, 2H), 7.56 (s, 1H), 7.72 (d, 2H).

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

Reference:
Patent; Arizona Board of Regents for and on Behalf of Arizona State University; US2011/301351; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39861-21-7, These common heterocyclic compound, 39861-21-7, name is 4-(5-Chloro-1H-benzo[d]imidazol-2-yl)aniline, 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.

General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below.

Statistics shows that 4-(5-Chloro-1H-benzo[d]imidazol-2-yl)aniline is playing an increasingly important role. we look forward to future research findings about 39861-21-7.

Reference:
Article; Janupally, Renuka; Jeankumar, Variam Ullas; Bobesh, Karyakulam Andrews; Soni, Vijay; Devi, Parthiban Brindha; Pulla, Venkat Koushik; Suryadevara, Priyanka; Chennubhotla, Keerthana Sharma; Kulkarni, Pushkar; Yogeeswari, Perumal; Sriram, Dharmarajan; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5970 – 5987;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-50-2, The chemical industry reduces the impact on the environment during synthesis 3034-50-2, name is Imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a stirring solution of NaH (1.25 g, 52.1 mmol) in DMF (65 mL) was added SM1 (5 g, 52.1 mmol) followed by iodomethane (8.13 g, 57.3 mmol) at 0 C. Thereaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with DCM. Combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain crude product, which was purified by silica gel column chromatography eluting with 5% MeOH/ DCM to compound 1(1.95 g, 34%) as a yellow solid. LC-MS: m/z = 111[(M+1)].

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, Imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; KESICKI, Edward A.; WANG, Ce; PATANE, Michael A.; KLUGE, Arthur F.; VAN DRIE, JR., John H.; (121 pag.)WO2016/44777; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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 33543-78-1 as follows.

Compound 52 was alkylated in sequence with ethyl bromoacetate, isopentyl iodide, and iodomethane to give compound 55. Hydrolysis of compound 55, followed by a treatment with TMS-Eto-acetylene, gave the cyclic anhydride 57. Reaction of compound 57 with diethyl malonate gave compound 58, which coupled with compound 11 to yield the compound 215.

According to the analysis of related databases, 33543-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERMUNE, INC.; US2009/257979; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 20034-02-0, name is (6-Methyl-1H-benzo[d]imidazol-2-yl)methanol, molecular formula is C9H10N2O, 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. Application In Synthesis of (6-Methyl-1H-benzo[d]imidazol-2-yl)methanol

N-Methyl-2-methanol-5-methylbenzimidazole 48 was prepared according to using the procedure by Harisha et al. [28]. A solution of 5-methyl-(1H-benzimidazole-2-yl)-methanol 25 (1.62 g, 0.01 mol), and sodium hydroxide (0.40 g, 0.01 mol) were stirred in dry acetone (30 mL) was stirred for 30 min. Then, iodomethane (1.41 g, 0.01 mol) was added to the mixture and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. Then, wash the solid with cold water (100 mL) and then aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (FAS37) as a brown powder Yield 46%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20034-02-0, its application will become more common.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 OI-14a (4 g, 36.36 mmol, 1.0 eq) in chloroform (40 mL) was added NBS (7.12 g, 40 mmol, 1.1 eq). The mixture was stirred at 70 C. for 3 h. Then the mixture was cooled to room temperature and diluted with a saturated aqueous solution of Na2CO3 (50 mL) and DCM (100 mL). The organic layer washed with brine and water, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give OI-14b (333 mg, 4.8%).

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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 solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (30 mL) under an argon atmosphere were added potassium carbonate (6.70 g, 48.61 mmol) and 4-(trifluoromethyl)-1H-imidazole (1.7 g, 12.76 mmol) at room temperature. The reaction mixture was stirred at 50 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H- imidazol-1-yl) pyridine (1.4 g, 46%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.65 (s, 1H), 8.45 (s, 1H), 8.44 (s, 1H), 4.11 (s, 3H); LCMS: 288.8 (M+1); (column; X-Select CSH C-18 (50 ¡Á 3.0 mm, 3.5 mum); RT 3.46 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/ CH2Cl2 (Rf: 0.4).

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

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[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 312-73-2, Formula: C8H5F3N2

General procedure: mixtureof benzimidazole derivative (0.01 mol, insoluble in H2O) and correspondingacid (0.01 mol, insoluble in H2O) in absolute methanol (25 ml)was stirred at 65 C for 1-3 h. The solvent was distilled off, and theresidue was multiply washed with diethyl ether and dried (24 h) overP2O5 at ~0.01 Torr to afford viscous liquids or powders (soluble in water).Compounds 14, 15 were prepared by the reaction of ion exchange undersimilar conditions for 7-8 h.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Adamovich, Sergei N.; Mirskova, Anna N.; Mirskov, Rudolf G.; Lopyrev, Valentin A.; Mendeleev Communications; vol. 22; 6; (2012); p. 330 – 331;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem