Month: June 2021

Reference of 288-32-4, 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. 288-32-4 name is 1H-Imidazole, 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.

To a mixture of 1H-Imidazole (50 g, 0.73 mol) in DMF (200 mL) was added NIS (328 g, 1.46 mol) portionwise, the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was poured in sat. Na2CO3 solution, filtered, the residue was washed with water and dried to give 150 g of 2,4,5-triiodo-1H-imidazole (Yield=46%).

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

Reference:
Patent; Genentech, Inc.; US2012/245144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, 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 3304-70-9, COA of Formula: C7H8N2O4

1H-Imidazole-4,5-dicarboxylic acid dimethyl ester (1.5 g, 8.15 mmol, 1 equiv. ) was dissolved in MeOH (10 mL) and benzyl bromide (1.16 mL, 9.77 mmol, 1.1 equiv.) before sodium hydride (360 mg, 1.1 equiv., 60% dispersion) and sodium iodide (200 mg) was added. The reaction was stirred for 16 hours before being quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (2 x 30 mL) and the organic layer washed several times with water (4 x 30 mL), brine solution (50 mL). It was dried over Na2S04, filtered and concentrated in vacuo. 1-Benzyl-1H- imidazole-4,5-dicarboxylic acid dimethyl ester 254 (2.01 g, 90 %, 7.33 mmol). ¹H NMR (300 MHz) CDC13 No. 7.58 (s, 1 H), 7.33 – 7.42 (m, 3 H), 7.14 – 7.18 (m, 2 H), 5.41 (s, 2 H), 3.92 (s, 3 H), 3.84 (s, 3 H). MS: 275.1 (M+1)

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

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; CHEN, Xiaowu; FARDIS, Maria; JABRI, Salman, Y.; JIN, Haolun; KIM, Choung, U.; METOBO, Sanuel, E.; MISH, Michael, R.; PASTOR, Richard, M.; WO2005/117904; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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: (I) 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (3)(1.0 g; 4.0 mmol) was dissolved in DMF (20 ml), cooledat 0 C and under N2-atmosphere NaH (0.14 g; 6.0 mmol)was added to the solution. The suspension was stirred for30 min and cooled to -35 to -40 C. After N?,N-sulfonyldiimidazole(1.2 g; 6.0 mmol) in DMF (12 ml) was droppedto the reaction mixture and stirred for 30 min again at-40 C. MeOH was added (0.8 ml) to the solution andstirred for 30 min at -40 C. The solution was poured intoice-water (200 ml). The precipitate was filtered, washedwith cold water to get the white crystalline product 11(1.2 g; 80%). M.p.: 97-98 C; lit. m.p. (Vatle and Hanessian1996): 98-99 C; Rf = 0.70 (EtOAc-hexane 1:1).(II) From 3 (25.0 g; 96.0 mmol) the yield was 84% (31.5 g).

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagy, Adrienn; Csordas, Barbara; Zsoldos-Mady, Virag; Pinter, Istvan; Farkas, Viktor; Perczel, Andras; Amino Acids; vol. 49; 2; (2017); p. 223 – 240;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-1H-benzo[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. Formula: C7H5BrN2

[00586] A. tert-Buty 5-bromo-lH-benzo[d]imidazole-2-carboxyIate. A solution of 5-bromo-lH-benzimidazole (1.06 g, 5.38 mmol), di-tert-butyl dicarbonate (1.3 g, 5.91 mmol), triethylamine (0.9 mL, 6.45 mmol) and dimethylaminopyridine (few crystals) in anhydrous tetrahydrofuran (15 mL) was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes) to provide the desired product (0.85 g, 54%) as a white solid. MS (ESI) m/z 297.3 [M+l]+.

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

The starting material was prepared as follows: Diethyl azodicarboxylate (160 mg, 1.4 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (261 mg, 0.7 mmol), (prepared as described for the starting material in Example 22), triphenylphosphine (367 mg, 1.4 mmol) and 2-(imidazol-1-yl)ethanol (94 mg, 0.84 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (42 mg, 0.7 mmol) was added and the solvent was removed by evaporation. The residue was triturated with ether, the solid collected by filtration, dried under vacuum and purified by chromatography eluding with methylene chloride/methanol (9/1 followed by 8/2) to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (250 mg, 76%).

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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. HPLC of Formula: C12H12N2O2

Under ice-cooling, L-selectride (4.52 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (30 mL) solution containing (4R,6S)-6-(4-fluorophenyl)-1,1-dimethyltetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (1.03 g). Stirring was continued for 1 hour at the same temperature. A 5 N sodium hydroxide aqueous solution (686 muL) was added to the reaction solution, and stirring was continued for 20 minutes at 0 C., and next hydrogen peroxide solution (333 muL, 35% aqueous solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (356 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine was added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (30 mL) and triphenyl phosphonium bromide (1.2 g) were added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was cooled to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (817 mg) and triethylamine (951 muL) was added, and stirring was continued for 10 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum. Crude purification of the residue was conducted by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate?ethyl acetate/methanol). The resulting solid was suspended in ethyl acetate, and diethyl ether was added, and the resultant was left overnight at 4 C. By filtering, the title compound (860 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 462 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.45 (s, 3H), 1.58 (s, 3H), 1.82-1.93 (m, 1H), 2.02-2.14 (m, 2H), 2.29 (s, 3H), 2.33-2.44 (m, 1H), 3.84 (s, 3H), 3*94 (dd, J=12.0, 5.2 Hz, 1H), 5.16 (d, J=9.6 Hz, 1H), 6.77 (s, 1H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 6.98-7.03 (m, 2H), 7.17 (d, J=8.4 Hz, 1H), 7.28-7.31 (m, 3H), 7.53 (d, J=2.0 Hz, 1H), 7.69 (d, J=1.2 Hz, 1H).

The synthetic route of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 22884-10-2, These common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 50 mL flask was added 4-chloro-orthozilidine 1c (1 mmol), alpha-bromo-tert-butyl ketone (1.2 mmol), and potassium carbonate (1.5 mmol), and reacted at 45 C, The reaction solvent was chloroform (20 mL). After reacting for 2 hours, diphenylmethylphosphine (1.5 mmol) was further added, and the reaction was carried out at 30 C. After the reaction was continued for 3 hours, the solvent chloroform was removed under reduced pressure. The residue was transferred to a solution of triphenylphosphine (2.5 mmol) and iodine (2.5 mmol) in chloroform (15 mL). After reacting for 2 hours, after completion of the reaction, the solvent chloroform was removed under reduced pressure. Residue column chromatography gave 0.223 g of the title compound 2c. The yield was 71%.

Statistics shows that 2-(1H-Imidazol-1-yl)acetic acid is playing an increasingly important role. we look forward to future research findings about 22884-10-2.

Reference:
Patent; China Three Gorges University; Wang Long; Yang Qingqing; Li Yongshuang; Li Dejiang; (8 pag.)CN109265448; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7, 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2-bromo-l-(2,4-difluorophenyl)ethanone (63.1 g, 269 mmol) and 4-cyano- IH- imidazole (25.0 g, 269 mmol, 1.0 eq) in acetonitrile (200 mL) was added NN-diisopropylethylamine (93.81 mL, 69.4 g, 537 mmol, 2.0 eq) and zinc(II) chloride (3.66 g, 26.86 mmol, 0.10 eq) at 30C. The reaction mixture was stirred at 70 C for 12 hours. The reaction mixture was filtered and concentrated in vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate =1 :1) to give a mixture of desired 3-[2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile and its regioisomeric by-product 1- [2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile as an approximately 40:60 mixture (total : 30.0 g, combined yield: 45%).

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; MILLER, Ricarda; GENIX, Pierre; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; (124 pag.)WO2018/60074; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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: Two different solutions for feeds A and B were separately prepared in 2 mL vial equipped with a Teflon septum and magnetic stir bar. Feed A: [Ir(dtbbpy)(ppy)2][PF6] (2.00 lmol, 0.01 equiv) and Boc-Pro-OH (0.3 mmol, 1.5 equiv) in 1 mL of DMA; Feed B: NiCl2 glyme (0.02 mmol, 0.1 equiv), 4,4′-di-tert-butyl-2,2′-bipyridyl (0.03 mmol, 0.15 equiv), the corresponding aromatic halides (0.20 mmol, 1.0 equiv), DBU (0.3 mmol, 1.5 equiv) in 1 mLof DMA. The two solutions were degassed by bubbling nitrogen stream for 20 min. Feeds A and B were injected simultaneously into the photoreactor, mixed in a T-mixer, and passed through a 10 mL residence time coil (0.8 mm inner diameter, 4 m length, fluoropolymer tube) irradiated with blue LED 450 nm and heated atthe indicated temperature. The reaction mixture collected from the output was diluted with saturated aqueous NaHCO3 solution,extracted with Et2O (3 10 mL). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentratedin vacuo. Purification of the crude product by flash chromatography on silica gel using as eluent heptane/ethyl acetate afforded the desired product.

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

Reference:
Article; Abdiaj, Irini; Alcazar, Jesus; Bioorganic and Medicinal Chemistry; vol. 25; 23; (2017); p. 6190 – 6196;,
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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H10F3N3

General procedure: A suspension of methyl 4-methyl-3-(4-(pyridin-3-yl)thiazol-2-ylamino)benzoate (325 mg, 1mmol) and 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (241 mg, 1 mmol) in 10 mL anhydrous THF was cooled to -20 C, a solution of tBuOK (672 mg, 6 mmol) in 10 mL anhydrous THF was added. The reaction mixture was warmed to room temperature slowly and stirred at r.t. for 10 h. The reaction was quenched by adding brine, extracted by E.A., the organic phase were combined, then remove the solvent and the residue was purified by column chromatography on silica gel to afford the title product as a white solid (459 mg, 86%).

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Deping; Zhang, Zhang; Lu, Xiaoyun; Feng, Yubing; Luo, Kun; Gan, Jirong; Yingxue, Liu; Wan, Junting; Li, Xiang; Zhang, Fengxiang; Tu, Zhengchao; Cai, Qian; Ren, Xiaomei; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 21; 7; (2011); p. 1965 – 1968;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem