Tag: M.W=100-200

Application of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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.

Step 1: To a stirred mixture of DMF (15 mL) and NaH (60% dispersion in mineral oil, 539 mg, 21 mmol) at 0C under argon was added 4-bromo-1H-imidazole (3 g, 20 mmol) in one portion. The mixture was stirred for 5 min at 0C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.3 mL, 24 mmol) in DMF (3 mL) was added dropwise. Afterstirring at 0 C for 1 h, the mixture was warmed slowly to rt and stirred for 6 h. The mixture was then partitioned betweenEtOAc (100 mL) and water (50 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4, filtered,and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography(eluting with a gradient of 100% hexanes to 100% EtOAc) to afford a regioisomeric mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as an oil (2.9 g, 53%).LCMS (ESI) m/z 277 and 279 (M+H)+. Step 1: To a mixture of the regioisomers 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole and 5-bromo,-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (643 mg, 2.3 mmol) from Step 1 of Example 32, acetamide(275 mg, 5.0 mmol), and Cs2CO3 (1.5 g, 5 mmol) in 1,4-dioxane (7 mL) was added N,N?-dimethylethylenediamine (500mL, 5 mmol). Argon was bubbled into the mixture for 5 min followed by the addition of CuI (221 mg, 1.1 mmol). Argonwas bubbled into the mixture for an additional 5 min. Then the reaction vessel was sealed and the mixture was heatedat 100 C for 15 h. The mixture was cooled to rt, then partitioned between EtOAc (100 mL) and water (50 mL). TheEtOAc layer was separated, washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc toafford a mixture of regioisomers N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)acetamide and N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)acetamide (170 mg, 29%) as an oil. LCMS (ESI) m/z 256 (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 4-Bromo-1H-imidazole, its application will become more common.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-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 33468-69-8, Recommanded Product: 4-(Trifluoromethyl)-1H-imidazole

To a stirred solution of 4-(trifluoromethyl)-1H-imidazole (OC, 0.94 g, 6.91 mmol) in THF (20 mL), K2C03 (1.14 g, 8.29 mmol) was added and the reaction mixture was stirred at RT for 15 min. To the resulting reaction mixture, 2-bromo-1-(4-fluorophenyl)ethan-1-one (CH, 1.50 g, 6.91 mmol) was added and the reaction mixture was stirred at RT for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (40% EtOAc/hexane) to afford compound OD (1.2 g, 67.0%) as an off-white solid.1H NMR (400 MHz, DMSO-d6): _ 8.14-8.10 (m, 2H), 7.76 (d, / = 17 ‘.2 Hz, 2H), 7.44 (t, J = 8.8 Hz, 2H), 5.80 (s, 2H); LC-MS: m/z 272.95 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Weight ligand L0 (1 mmol, 179 mg), 1 mmol ZnCl2 (136 mg) intocapacity polytetrafluoroethylene reactor, add 12 mL CH3OH, stirand dissolve. After adding Et3N, the kettle was placed in a reactionat 140 C for 24 hours, and then achromatous crystals were obtain.Yield 33 % (based on L0). Elemental analyses calc (%) for 1: C, 47.97;H, 4.03; N, 13.98. Found: C, 47.05; H, 3.86; N, 14.33. IR (KBr, cm1):3314(s), 2421(m), 1622(m), 1521(m), 1467(m), 1250(m), 1102(m),1001(m), 908(m), 761(s), 559(m).

According to the analysis of related databases, 3012-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Shixiong; Liu, Lingmei; Deng, Yan; Huang, Yuanhao; Chen, YuFeng; Liao, Beiling; Polyhedron; vol. 174; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1, 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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Prepared above 5-bromo -1H- benzo [d] imidazole (3.25g, 22.1mmol) in solution in THF (65 mL) of, Boc2O (5.79g, 26.5mmol), Et3N (3.35,33.15mmol) and DMAP (270mg, 2.21mmol) was added. The mixture was stirred for 4 hours at room temperature, then diluted with water (200mL), and extracted with ethyl acetate (200mL). The organic layer was washed with water (2 ¡Á 100 mL) and brine (100 mL), dried over Na2SO4, and concentrated to give 0601-187 as an oil (4.8g, 98%).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Nitro-1H-imidazole

Step A: To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.6 mmol) in acetonitrile (18 mL) was added iodomethane (1.32 mL, 21.2 mmol) and the mixture was heated in a sealed vial at 60 C. overnight. The mixture was filtered washing with acetone. The filtrate was concentrated under reduced pressure, and the residue was diluted with hot isopropanol and cooled, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform and filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with propan-2-ol and collected by filtration to afford 1-methyl-4-nitro-1H-imidazole (1.03 g, 46%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) delta 8.37 (d, J=1.1 Hz, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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 mixture of 4-bromopyridin-2-ol (0.49 g, 2.82 mmol), l-tetrahydropyran-2-yl-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole (0.86 g, 3.10 mmol), granular K2CO3 (1.17 g, 8.47 mmol), PdCl2(dppf) (0.10 g, 0.14 mmol), l,4-dioxane (12 mL), and H20 (5 mL) was stirred at 80 C under an argon atmosphere overnight. The reaction mixture was diluted with brine (40 mL), and extracted with dichloromethane (2 x 60 mL). The extracts were combined, dried over anhydrous MgS04, filtered, and the filtrate was concentrated to dryness on a rotovap. The crude material was purified on a silica gel column (methanol in dichloromethane, 0-50%) to afford the desired 4-(l-tetrahydropyran-2-ylpyrazol-4-yl)pyridin-2-ol (0.56 g, 81%) as a white, fluffy powder. LC-MS 246.3 [M+H]+, RT 1.05 min.

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of thiazolidinedione (6a, 0.5mmol), 1-methyl-1H-benzo[d]imidazole-2-carbaldehydes (10a, 0.55mmol) in ethanol (4mL) was added catalytic amount of piperidine. The reaction mixture was refluxed until complete conversion as observed by TLC. After cooling, the precipitates were filtered, washed and recrystalized with ethanol, to obtain pure (Z)-5-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)thiazolidine-2,4-dione derivative 11a as yellow solids. All the other compounds 11b?t were obtained in a similar reaction procedure of 11a in moderate to high yields.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sharma, Pankaj; Srinivasa Reddy; Thummuri, Dinesh; Senwar, Kishna Ram; Praveen Kumar, Niggula; Naidu; Bhargava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 608 – 621;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-19-9, These common heterocyclic compound, 17289-19-9, name is Methyl 1-methyl-1H-imidazole-4-carboxylate, 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 methyl 1-methyl-1H-imidazole-4-carboxylate (14.3 mmol, 2 g) in CCl4 (40 mL), NBS (15.3 mmol, 2.72 g) and AIBN (0.715 mmol, 117 mg) were added. The reaction mixture was heated for 4 h at 60 C and then cooled to RT. The solvent was evaporated. The reaction crude was purified by flash chromatography over silica gel using an elution of 8% methanol in ethyl acetate to afford 529 mg (Yield: 17%) of the title compound 18. 1H NMR (400 MHz, CDCl3): delta 7.59 (1H, s), 3.91 (3H, s), 3.67 (3H, s); ESI-MS: m/z 219 [M + H]+

The synthetic route of 17289-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 9; (2016); p. 1117 – 1130;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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 mixture of ethyl lH-imidazole-2-carboxylate (1.96 g, 14.0 mmol), 3,5-dichloro-2- fluoropyridine (1.80 g, 10.8 mmol), potassium carbonate (2.24 g, 16.2 mmol), and NMP (54 mL) was heated at 115 0C for 6 h, allowed to cool to rt, and then poured into EtOAc (200 mL). The mixture was washed with water (200 mL), washed with brine (200 mL x 2), dried, filtered, concentrated, and purified by silica gel chromatography (4:1–>1 :1; hexanes: EtOAc) to give ethyl l-(3,5-dichloropyridin-2-yl)-lH-imidazole-2- carboxylate. 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, IH), 8.62 (d, IH), 7.78 (d, IH), 7.36 (d, IH), 4.15 (q, 2H), 1.13 (t, 3H); LCMS: 286.1 (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 Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; KALYPSYS, INC.; WO2009/117421; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

The amine precursor 16 (100,7 mg, 0.240 mmol, 1 eq.) was dissolved in 1 ml of DMF, acetylimidazole (31.7 mg, 0.288 mmol, 1.2 eq) and DIPEA (0.090 ml, 0.48 mmol, 2 eq.) wereadded to the solution. After stirring the mixture for 48h at room temperature, the solvent was evaporated under reduced pressure to give the corresponding crude, which was purified by HPLC using a gradient of 5percent to 95percent v/v acetonitrile in 0.1percent aqueous solution of formic acid to yield the titled compound. Yield: 91 mg, 0.187 mmol (78percent). 1H NMR (400 MHz, CDCI3) 9.25 (1H, 5), 8.70 (1H, 5), 7.97 (1H, t, J=6.5 Hz), 7.15 (1H, d, J=7.5 Hz), 6.83-6.80 (2H, m),6.72 (1H, d, J=8.8 Hz), 4.92-4.88 (1H, m), 4.57 (1H, 5), 4.52-4.42 (2H, m), 4.26-4.14 (2H, m), 3.59 (1H, dd, J=2.9, 11.1 Hz), 2.53-2.45 (4H, m), 2.24-2.17 (1H, m), 1.85 (3H, 5), 0.83 (9H, 5); 13C NMR (101 MHz, ODd3) O 171.8, 171.2, 155.9, 150.7, 148.1, 132.8, 131.7, 131.0, 124.2, 120.6, 117.1, 70.3, 58.1, 57.7, 57.1, 39.8, 35.5, 34.8, 26.3, 22.6, 16.0. HRMS (ESI) m/z: [M+H] calculated for: C24H32N405S: 488.21; observed: 484.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; MANIACI, Chiara; HUGHES, Scott J.; TESTA, Andrea; (111 pag.)WO2018/189554; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem