Month: May 2021

23328-88-3, name is 2-Bromo-4-methyl-1H-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. Recommanded Product: 23328-88-3

Intermediate 1D: 2-Bromo-1-(3-methoxy-2-nitro-phenyl)-4-methyl-1H-imidazole 2-bromo-4-methyl imidazole (3.7 g, 23.4 mmol) and 2-fluoro-6-methoxy-nitrobenzene were dissolved in DMF (80 mL). To this was then added potassium carbonate (6.3 g, 46.8 mmol). The reaction was heated to 90 C. for 16 hrs then poured into water and extracted with ethyl acetate. The organic layer was separated and washed with water then brined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the crude purified by flash chromatography on silica gel in 20:1 ethyl acetate/methylene chloride. A tan solid (2.6 g) was recovered. MS (ES) m/z 311.9 [M+1]+

The synthetic route of 23328-88-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELBION GMBH; WYETH; US2009/143367; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, Product Details of 39021-62-0

General procedure: Into a round-bottom flask, equipped with a condenser and containing a suspension of 6 (2.0 mmol, 1 equiv) in ethanol (15 mL), was introduced the aldehyde (2.2 mmol, 1.1 equiv) and two drops of concentrated HCl. The reaction mixture was stirred and heated at 80 C for approximately 18 h. While cooling down the crude mixture in an ice bath, a precipitate was formed which was subsequently filtered off and washed with both water (2 × 10 mL) and cold ethanol (3 × 15 mL). The solid residue was then dried in vacuum at 60 C.

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, 1-Methyl-1H-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pevet, Isabelle; Brule, Cedric; Tizot, Andre; Gohier, Arnaud; Cruzalegui, Francisco; Boutin, Jean A.; Goldstein, Solo; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2517 – 2528;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2620-76-0, The chemical industry reduces the impact on the environment during synthesis 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, I believe this compound will play a more active role in future production and life.

[122] 1 -phenyl-2-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl)-1 H-benzo[d]imidazole (5): A mixture of Compound 4 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533g, 2.1 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)CI2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (KOAc) (0.393 g, 4mmol) in 1 ,4-dioxane (20 ml) was heated at about 80 C under argon overnight. After cooling to RT, the whole was diluted with ethyl acetate (80 ml) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3: 1 ) to give a white solid 5 (0.64 g, in 81 % yield).

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-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; WO2014/93353; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 312-73-2, These common heterocyclic compound, 312-73-2, name is 2-(Trifluoromethyl)-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.

General procedure: A solution of this chloromethyl ester (1.8 mmol) in N,N-dimethylformamide (4 ml) was treated with the 2-substituted benzimidazoles (1.8 mmol) and cesium carbonate (2.8 mmol). The mixture was stirred for 3 h at r.t. and partitioned with water and ethyl acetate (20 ml). The aqueous layer was further extracted with ethyl acetate (20 ml) and the combined organic layers washed with brine (20 ml), dried (sodium sulfate), filtered and concentrated. Flash chromatography with ethyl acetate provided the desired product as colored oil.

Statistics shows that 2-(Trifluoromethyl)-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 312-73-2.

Reference:
Article; Sengupta, Prabal; Puri, Chetan S.; Chokshi, Hemant A.; Sheth, Chetana K.; Midha, Ajay S.; Chitturi, Trinadha Rao; Thennati, Rajamannar; Murumkar, Prashant R.; Yadav, Mange Ram; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5549 – 5555;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 256519-10-5, name is 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5FN2O, 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. Recommanded Product: 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one

Preparation 47 2-Chloro 4-fluoro-1H-1,3-benzimidazole STR92 The title compound was prepared by the method of Preparation 25 from 4-fluoro-1,3-dihydro-2H-1,3-benzimidazole-2-one [see Preparation 46]. 1 H-NMR (d4-MeOH) delta: 7.32 (1H, d), 7.28 (1H, m), 7.00 (1H, t).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 256519-10-5, its application will become more common.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 three-necked 250 mL round bottom flask equipped with thermometer, condenser, and stir bar, was charged with toluene (75 mL), ethyl 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoate (3 g, 9.0 mmol, 1 eq.), and 5-(4-methyl)-1H-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (2.82 g, 11.7 mmol, 1.3 eq.). The suspension was warmed up and 6.8 mL AlMe3 (2 M in toluene, 13.8 mmol, 1.5 eq.) was added. The entire mixture was then being refluxed for 5 hrs until the ester disappeared and the process was monitored by an HPLC. After the mixture was cooled down, excess trimethyl aluminum was quenched with aqueous sodium hydroxide. The product was isolated by filtration and dried under vacuum affording 4.32 g (91%) nilotinib with 99.3% purity (HPLC). Results of other examples with different ratio of starting material are listed in the Table 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; FORMOSA LABORATORIES, INC.; Hung, Jui-Te; Chen, Wen-Chin; US9187452; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 870837-18-6 as follows. name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Compound B2 (R2 = H, 1.5 g, 5.6 mmol, synthesized as in Tett. 1987, 43, 5125) in 40 ml of anhydrous THF at 0 0C was treated with NaH (0.25 g, 5.9 mmol, 60% in mineral oil). After 20 min, B1 (R8 = H, R10 = 3-MeO-Phenyl, R9 = 4-(4- Methylimidazol-1-yl), 1.Og, 4.62 mmol) was added and the reaction warmed to ambient temperature. After 18 h, the reaction mixture was quenched with saturated aqueous NH4CI and extracted with EtOAc (2x). The combined organic layers washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (gradient 1? 10 % MeOH/CH2CI2) provided 1.2 g (81 %) of B3 (R8 = H, R2 = H, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol-1-yl)).

According to the analysis of related databases, 870837-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2009/20579; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-22-5, 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. 934-22-5 name is 6-Aminobenzimidazole, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 50995-95-4, The chemical industry reduces the impact on the environment during synthesis 50995-95-4, name is 2-Propylimidazole, I believe this compound will play a more active role in future production and life.

Preparation of 2-chloro-6-(2-propylimidazol- 1 -vDpurine. Method 1: 2,6-Dichloropurine (0.38 g, 2 mmol) and 2-propylimidazole (1.32 g, 12 mmol) were dissolved in freshly distilled DMF (10 mL), and the mixture was stirred at 65 C for 20 h. Volatiles were evaporated in vacuo, and the residue was dissolved EPO in 0.1 N NaOH/H2O//CH2Cl2 (100 mL/50 mL). The organic phase was extracted with 0.1 N NaOHZH2O (3 x 50 mL). The combined aqueous phase was washed with CH2Cl2 (2 x 50 mL) and neutralized with CO2. The precipitated solid was filtered and washed (H2O) to give 2-chloro-6-(2-propylimidazol-l-yl)purine (0.38 g, 72%): mp 224.5-225 C; UV (MeOH) max 215, 288 nm (epsilon 25 800, 16 700), min 332, 241 nm (epsilon 2500, 4500); 1H NMR (500 MHz, DMSO-J6) delta 14.04 (br s, IH), 8.69 (s, IH), 8.43 (s, IH), 7.06 (s, IH,), 3.12 (t, J= 7.5 Hz, 2H), 1.72 (sext, J= 7.3 Hz, 2H), 0.95 (t, J= 7.3 Hz, 3H); 13C NMR ( 125 MHz, DMSO-^6) delta 157.3, 151.7, 150.2, 147.2, 146.6, 128.9, 122.5, 121.1, 32.4, 21.5, 14.5; HRMS m/z 262.0723 (M+ [Ci1H11ClN6] = 262.0734). Anal. Calcd for CnHnClN6: C, 50.29; H, 4.22; N, 31.99. Found: C, 50.02; H, 4.28; N, 31.64.

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-Propylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRIGHAM YOUNG UNIVERSITY, TRANSFER TECHNOLOGY OFFICE; WO2006/138396; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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.

a) (3H-Imidazol-4-ylmethyl)-(4-trifluoromethoxy-phenyl) -amine; To a solution of 4-trifluoromethoxyaniline (0.89 g, 5 mmol) in methanol (5 ml) was added 4-formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 600C the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by column filtration (heptane/ ethyl acetate= 1:1) to yield a light yellow liquid ( 1.0 g, 78%) ; MS (ISP): 258.1 ((MH-H)+-).

Statistics shows that Imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 3034-50-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/46757; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem