Tag: M.W=200-300

Synthetic Route of 53484-16-5, 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 53484-16-5 as follows.

A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2,3-dihydro-1 ,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mixture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator andconcentrated. The residue was purified by prep HPEC toyield the desired product (Compound B).

According to the analysis of related databases, 53484-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole, 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 6478-79-1, Application In Synthesis of 5,6-Dichloro-2-methylbenzimidazole

General procedure: To extend the scope of the 2-methyl-1H-benzimidazole substrates for our cascade reaction, we nextexamined the reaction of 2-fluorobenzonitrile (2a) with a variety of 2-methyl-1H-benzimidazolederivatives 1 under the conditions (Cs2CO3, DMSO, 120 C). The results are shown in Table 2. As shown in Table 2, almost all of the tested combinations successfully produced the desiredbenzimidazo[1,2-a]quinolines 8ba-8la with moderate to good isolated yields, though an undeniableamount of overreaction product 9 was isolated in most entries. Unsymmetrical 1H-benzo[d]imidazolessuch as 1b, 1e, 1f and 1g exist as an equilibrium mixture of their tautomers. Therefore, the SNAr sequenceof our cascade reaction with these substrates theoretically provides a regioisomeric mixture of thecorresponding adducts. Our survey revealed that the regiochemical outcome is highly controlled uponutilizing 1e, 1f and 1g having a substituent at the 4-position to give 8ea, 8fa and 8ga without detectingtheir regioisomers (entries 5-7). However, no reigioselectivity was observed with the cascade reactionwith 1b bearing methyl substituent at the 5-position (entry 2). These results suggest to us that the lesssterically congested nitrogen atom of 1H-benzo[d]imidazoles preferably reacted with 2-fluorobenzonitrile(2a) in the SNAr reaction. 2-Methyl-1H-benzimidazole derivatives 1h, 1i, and 1j, having an electrondonating group (-CH3, -OCH3,-SCH3), reacted with 2a to give 8ha, 8ia, and 8ja in modest yields underthe conditions, respectively (entries 8-10). When the benzimidazoles 1k and 1l possessing an electronwithdrawing group (-CN, -CO2Et) at the 2-methyl group were treated with 2a under the conditions, alarge amount of insoluble unidentified product was produced. In these reactions, the desired cascadeproduct 8la was not detected while the cascade product 8ka was isolated in a modest yield (entries 11 and12). The cascade products 8ka and 8la were obtained in good yields upon replacing Cs2CO3 with K2CO3.(entries 11 and 12). In our SNAr/Knoevenagel cascade reaction with 1k and 1l, we found the Knoevenagelcondensation between aldehydes and the active methylene of 1k and 1l occured preferably to the SNArreaction in the first step, and the desired cascade adducts could not be obtained.14 These comparativeresults indicate that the SNAr reaction occured preferably to the Dieckmann-Thorpe type reaction in thepresent cascade reaction upon fine-tuning the base used.

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; Kato, Jun-Ya; Ito, Yutaro; Ijuin, Ryosuke; Aoyama, Hiroshi; Yokomatsu, Tsutomu; Heterocycles; vol. 93; 2; (2016); p. 613 – 627;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1008360-84-6, 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. 1008360-84-6 name is 5-Bromo-6-fluoro-1H-benzo[d]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 solution of 5-bromo-6-fluoro-1H-benzimidazole (2.2 g, 10.2 mmol) in tetrahydrofuran (40 mL) at 0 degrees C. was added sodium hydride (0.5 g, 12.3 mmol) as a solid in 2 portions. After stirring 30 min. at 0 C., trityl chloride (3.7 g, 13.3 mmol) was added, followed by tetrabutylammonium iodide (catalytic). The reaction was heated at reflux for 1.5 h, then was allowed to cool and was quenched with water. The mixture was extracted with chloroform (3×) and the combined organics were dried over sodium sulfate and concentrated in vacuo. The residue was triturated with hot ethyl acetate and the solid was isolated via filtration and dried under vacuum. This provided the product as a mixture of trityl regioisomers, 5-bromo-6-fluoro-1-(triphenylmethyl)-1H-benzimidazole and 6-bromo-5-fluoro-1-(triphenylmethyl)-1H-benzimidazole.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-6-fluoro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 342789-81-5,Some common heterocyclic compound, 342789-81-5, name is 1-Butyl-3-methylimidazolium methanesulfonate, molecular formula is C9H18N2O3S, 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.

5.3-1-Butyl-3-methylimidazolium N-trifluoro-sulfonamidate [BMI.(CF3SO2)2N]A mixture formed by 1,3-dimethyl imidazolium methanesulfonate (BMI.CH3SO3) (4.26 g; 18.2 mmol), lithium N-trifluoro sulfonimidate (5.47 g; 19.1 mmol) and water (10.0 mL) was stirred at room temperature for 45 minutes. The resulting mixture, made up by two phases, was extracted with dichloromethane (3×15 mL). The combined organic extract was washed with water (1×20 mL) and dried with anhydrous sodium carbonate. The solvent was evaporated under vacuum and heated (80 C.), which produced the desired ionic liquid BMI.(CF3SO2)2N (7.33 g. 96% yield).

The synthetic route of 342789-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETROLEO BRASILEIRO S.A. – PETROBRAS; US2008/45723; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 92807-02-8, A common heterocyclic compound, 92807-02-8, name is Methyl 2-mercapto-1H-benzo[d]imidazole-4-carboxylate, molecular formula is C9H8N2O2S, 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 2-sulfanyl-1H-benzimidazole-4-carboxylate (prepared as described in WO2003/106430) (1.0g) in DMF (15 mL), were added potassium carbonate (700 mg) and methyl iodide (0.32 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (860 mg) as white powder.

The synthetic route of 92807-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; OTSU, Hironori; EP2746265; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 256518-97-5, 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 256518-97-5 as follows.

Step 5: Under nitrogen protection, 2-chloro-6-iodo-1H-benzimidazole (2.34 g, 8.4 mmol) was added to the reaction vessel.Isopropyl boric acid (0.81 g, 9.2 mmol), tetrakistriphenylphosphine palladium (0.05 g, 0.04 mmol),Potassium carbonate (1.74 g, 12.6 mmol), toluene 60 mL, ethanol 20 mL, and distilled water 20 mL were stirred at 120 C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, extracted with ethyl acetate and dried over MgSO 4The solvent was evaporated under reduced pressure, and then purified by silica gel column chromatography to afford compound 35-5 (1.26 g, 77%).

According to the analysis of related databases, 256518-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (23 pag.)CN109305943; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 72459-45-1, A common heterocyclic compound, 72459-45-1, name is 1-(2-Bromobenzyl)-1H-imidazole, molecular formula is C10H9BrN2, 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.

EXAMPLE 7 (COMPOUND 7) 2-Bromophenyl-1-(1-hydroxycycloheptyl)-1-imidazolylmethane A solution of lithium diisopropylamide in 100 ml of tetrahydrofuran was prepared at -30 C. from 5.1 g (50 mmol) of diisopropylamine and 30 ml (50 mmol) of n-butyllithium in hexane. 11.85 g (50 mmol) of N-(2-bromobenzyl)-imidazole were added dropwise to this solution at -78 C., stirring was carried out for half an hour and 5.6 g (50 mmol) of cycloheptanone were then added at this temperature. The reaction mixture was warmed up to room temperature in the course of 3 hours and worked up with water and methylene chloride. 12 g of crude product were obtained, and this product gave 5.5 g of an imidazole derivative of melting point 108 C. after recrystallization with cyclohexane/ethyl acetate.

The synthetic route of 72459-45-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4876354; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-65-4, 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 24134-65-4 as follows.

A solution of lambda/-methyl-lambda/-[2-(methylamino)ethyl]- 3,4-bis(methyloxy)benzenesulfonamide (50 mg; 0.17 mmol), prepared as Example 10a, and DIEA (43 uL; 0.25 mmol) in 2 mL of DCM was treated with 1 ,3-dimethyl-2- oxo-2,3-dihydro-1 /-/-benzimidazole-5-sulfonyl chloride (47 mg; 0.18 mmol). The solution was capped under nitrogen and stirred at room temperature overnight. The reaction was diluted to 10 mL with DCM and washed once each with 1 M NaHSO4, water, and sat’d aq. NaHCO3. The organic phase was dried over Na2SO4 and concentrated in vacuo to give 87 mg of the title compound as white amorphous solid. 92% purity by HPLC. LCMS (M+H = 513). 1 H NMR (DMSO-d6) delta 7.49 (m, 2H), 7.32 (m, 2H), 7.14 (m, 2H), 3.82 (s, 3H), 3.80 (s, 3H), 3.38 (s, 3H), 3.36 (s, 3H), 3.07 (bs, 4H), 2.67 (s, 3H), 2.66 (s, 3H).

According to the analysis of related databases, 24134-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/127505; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 84712-08-3,Some common heterocyclic compound, 84712-08-3, name is 5-Bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, molecular formula is C8H7BrN2O, 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 2: Synthesis of Intermediate 1-27.2 1-27.1 (4.41g, 19.42 mmol) and phosphoroxybromide (27.84g, 97.11 mmol) are stirred at 100C for 3h. The reaction mixture is diluted with iced water. The precipitate is filtered off and triturated with DIPE. Yield 89%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (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. 1093261-46-1, name is Methyl 5-bromo-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 5-bromo-1H-imidazole-4-carboxylate

A solution of methyl 4-bromo-1 /-/-imidazole-5-carboxylate (0.708 g, 3.5 mmol) was stirred in a solution of MeOH (20 mL) and 2N NaOH (20 mL, 40 mmol) at 40 0C for 4h, then additional 2N NaOH (20 mL, 40 mmol) was added and the reaction mixture kept at 40 0C for another hour. The reaction mixture was then acidified by addition of 1 M HCI (100 mL) and extracted with EtOAc. The organic extracts were dried (Na2SO4), and the solvent was evaporated to provide crude 4-bromo-1 /-/-imidazole-5- carboxylic acid (0.156g, 24%) as a white solid which was used without further purification.4-Bromo-lambda/-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1 /-/- imidazole-5-carboxamide trifluoroacetate was prepared in a similar manner as described herein from 3-{[3-aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5- chlorobenzonitrile (0.062 g, 0.20 mmol), 4-bromo-1 /-/-imidazole-5-carboxylic acid (0.038 g, 0.20 mmol), HATU (0.091 g, 0.24 mmol), DIPEA (0.042 ml_, 0.24 mmol) and DMF (2 ml_). Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.010 g, 8%) as a white solid. 1H NMR (400 MHz, DMSOd6) delta ppm 8.38 (br. s., 1 H), 7.82 (s, 2 H), 7.44 – 7.54 (m, 3 H), 7.38 (t, 1 H), 4.51 (d, 2 H). ES-LCMS: m/z 482.9, 484.9, 486.9 (M+1 ).

According to the analysis of related databases, 1093261-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem