Tag: M.W=100-200

Electric Literature of 615-15-6,Some common heterocyclic compound, 615-15-6, name is 2-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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: A 50 mL Schlenk tube equipped with a stirrer bar was charged with KI (16.6 mg, 0.1 mmol), benzotriazole (59.5 mg, 0.5 mmol), DMA (2 mL), and K2S2O8 (270 mg, 1 mmol) under air. The mixture was then stirred at 80 C for 6 h (TLC monitoring), poured into H2O (20 mL), and extracted with EtOAc (3 ×). Then the organic phase was evaporated under vacuum, and the crude product was purified by column chromatography [silica gel, PE-EtOAc (10:1 to 2:1)] to give a colorless oil; yield: 98 mg (96%);

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

Reference:
Article; Zhu, Zheng; Wang, Yufeng; Yang, Mingmeng; Huang, Ling; Gong, Jiuhan; Guo, Shengmei; Cai, Hu; Synlett; vol. 27; 19; (2016); p. 2705 – 2708;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-1-methyl-1H-imidazole

A solution of 1 mmol (0.167 g) of carbazole, 2 mmol (0.322 g) of 2-bromo-N-methyl-imidazole, benzotriazole 40 mol% (0.046 g) 20 mmol% (0.038 g) of copper iodide and 1.4 mmol (0.157 g) of potassium tertiary-butoxide were stirred in 6 mL of dimethylsulfoxide at 135C for 48 hours. The reaction mixture was allowed to cool and then water was added and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and then distilled under reduced pressure. The resulting brown solid was purified by silica column chromatography (using ethyl acetate and hexane). Finally, a colorless solid ligand 12 was obtained. The yield of the ligand 12 was 40%.

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:
Patent; Samsung Electronics Co., Ltd.; Samsung SD I Co., Ltd.; Das, Rupa Sri Rajini; Lee, Gang Mun; Noh, Chang Ho; Bae, Hay Jin; Rai, Birendra Kumar; Kravtsuk, Dmitry; (49 pag.)KR2016/12890; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

In a 10 mL vial was added N-(2,4-dimethyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.25 g, 0.55 mmol), 2-bromo-lH-imidazole (0.120 g, 0.82 mmol), and Cs2CO3 (0.444 g, 1.36 mmol) in dioxane (5 mL) to give a brown suspension. The reaction mixture was diluted with water (2 mL). Nitrogen was bubbled in for 20 min before Pd(PPh3)4 (0.063 g, 0.05 mmol) was added. The reaction was heated at 110 0C for 4h under microwave conditions. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC (MeCN/0.1% TFA in water). To the purified product was added HCl in Et2O (0.5 mL, 1 mmol) . The mixture was concentrated in vacuo to give the HCl salt of the title compound (10 mg, 4.2%). 1H NMR (DMSO-d6) delta 2.31 (s, 3 H), 2.36 (s, 3 H), 5.32 (s, 2 H), 7.18 (d, 2 H), 7.39 (s, 1 H), 7.45 ( br s, 1 H), 7.61 (s,2 H), 7.84 (s, 2 H), 7.96 (m, 3 H), 8.63 (d, 1 H), 9.90 (s, 1 H), 14.54 ( br s, 1 H). MS (M+H+) = 399.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); 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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., name: 2-Bromo-1H-imidazole

2-Bromo-lH-imidazole (100 mg, 0.680 mmol) was dissolved in DMF (2 mL) in a microwave vial in an ice bath and purged with nitrogen for 10 min. With the solution at 0 C, sodium hydride (60% dispersion in mineral oil) (62.6 mg, 1.565 mmol) was added and the solution was stirred for 10 min under nitrogen. A solution of 2-(bromomethyl)pyridine hydrobromide (207 mg, 0.816 mmol) in DMF (2 mL) was added dropwise to the reaction mixture. Once all reagents were added, the reaction mixture was allowed to warm to RT and stirred for 2 days under an atmosphere of nitrogen. The solvent was removed under reduced pressure. The crude product was dissolved in ethyl acetate (20 mL) and washed with brine (20 mL). The solvent was again removed from the organic layer under reduced pressure. The samples were dissolved in 1: 1 MeOH:DMSO (3 mL) and purified by MDAP (Method B). The solvent was evaporated in vacuo to give the title compound. LCMS (System B): tRET = 0.63 min; MH+ 238, 240.

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:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); 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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Quality Control of 1H-Benzo[d]imidazol-2-amine

Step 1: 1-Methyl-1H-benzimidazol-2-amine To a solution of 2-aminobenzimidazole (3.0 g, 0.0225 mol) in acetone (30 ml) was added KOH (6.32 g, 0.112 mol) followed by methyl iodide (3.51 g, 0.025 mol) and stirred at room temperature for 10 min. The reaction mixture was diluted with ethyl acetate and the organic layer washed with water, brine and dried over anhydrous Na2SO4 to afford crude residue which was column purified to yield the desired product: 1H NMR (300 MHz, DMSO-d6) delta 3.47 (s, 3H), 6.34 (br s, 2H), 6.82-6.92 (m, 2H), 7.06-7.09 (m, 2H); ESI-MS (m/z) 148.49 (M+H)+.

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:
Patent; Glenmark Pharmaceuticals S.A.; US2009/286811; (2009); 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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

(2-1) Take 5.07g (27mmol) of intermediate I into a 500mL round bottom flask with magnetons, add 350mL of ethanol, and put it into the collector type constant temperature heating magnetic stirrer, stir and stir to make the intermediate I completely dissolved; (2-2) Further, 0.12 g of palladium carbon was slowly added thereto, and the mixture was thoroughly mixed with the reaction liquid, and then hydrazine hydrate was added in three portions, each time 20.67 mmol (1 mL), a total of 3 mL (62 mmol), and the reaction was carried out for 6 hours, using a thin layer. Chromatographic TLC tracking detection; (2-3) The reaction is terminated, cooled and filtered, and then steamed to 25-30 mL, placed in a fume hood, heated to dryness to 15 mL of a white solid, and dried; (2-4) 40 mL of distilled water was added, and the mixture was stirred at normal temperature for 3 hours to remove hydrazine hydrate, suction filtered, and dried to give 3.88 g of white Intermediate II pure product, yield 91%.

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 2301-25-9.

Reference:
Patent; Fuyang Normal College; Liu Jie; Yang Chao; Zhou Ziyao; Wu Hai; Li Huiquan; (17 pag.)CN109206370; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 714273-83-3,Some common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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: First diacetyl piperazine diketone (DKP) and the aldehyde intermediate a or deuterium aldehyde compound b condensation reaction to form a heterocyclic compound c or deuterium-containing heterocyclic compound d;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Ding Zhongpeng; Wang Shixiao; Zhao Jianchun; Guan Huashi; (12 pag.)CN107286139; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-62-6, 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. 3034-62-6, name is 2-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The appropriate chloro-substrate (1 equiv) was dissolved in dioxane (0.04 M). Tripotassium phosphate (3.0 equiv), xantphos (0.05 equiv), palladium acetate (0.05 equiv) and the appropriate nucleophile (amine) (1.5 equiv) were then added. The reaction vessel was sealed and the mixture exposed to microwave radiation (150 0C, medium absorption setting) for 20 minutes. Upon completion the samples were filtered through a silica cartridge, washed with EtOAc and then concentrated in vacuo. The crude residue was then purified by preparative HPLC to give the desired products.

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-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-21-0, 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. 1003-21-0 name is 5-Bromo-1-methyl-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.

A mixture of a bromine substituted compound (1 eq.), boronic acid/boronate ester (1 eq.) in 1, 4-dioxane, and 2.5 eq. of 2M solution of potassium phosphate, was purged with Ar for 15 min, after which tetrakistriphenyl phosphine palladium (0.06 eq.) was added and the reaction stirred at 90 C overnight. After completion, the reaction mixture was filtered through Celite and evaporated to dryness. The residue was taken up in ethyl acetate, washed with water, followed by brine, then dried over anhydrous sodium sulfate and the solvent removed under reduced pressure. The crude product was purified by column chromatography or preparative HPLC to afford IV-9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; WALKER, Michael; LI, Leping; HAYDAR, Simon, Nicolas; (95 pag.)WO2020/51319; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]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.

To a solution of 2-chloro-1H-benzo[d]imidazole (3.0019 g, 19.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in 2.5 M sodium hydroxide solution (19.67 ml, 49.2 mmol, J. T. Baker) at 0 C. was added dimethyl sulfate (3.01 ml, 31.5 mmol, Riedel de Haen AG) dropwise. The reaction was allowed to stir for 1½ h. White precipitate was noted to form. The white precipitate was filtered, washed with water, and dried to give the title compound. LCMS showed product peak at 1.47 min (m+1=167.0). 1H NMR (400 MHz, DMSO-d6) delta ppm 3.80 (s, 3H) 7.21-7.28 (m, 1H) 7.28-7.35 (m, 1H) 7.59 (d, J=3.72 Hz, 1H) 7.61 (d, J=3.72 Hz, 1H)

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

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem