Month: August 2021

These common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, 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. Recommanded Product: (1-Methyl-1H-imidazol-2-yl)methanol

The starting material was prepared as follows: 1,1′-(Azodicarbonyl)dipiperidine (756 mg, 3 mmol) was added to a mixture of 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-hydroxy-6-methoxyquinoline (572 mg, 1 mmol), (prepared as described for the starting material in Example 20), tributylphosphine (300 mg, 3 mmol), and 2-hydroxymethyl-1-methylimidazole (134 mg, 1.2 mmol), (J. Chem. Soc. 1927, 3128-3136), in a mixture of methylene chloride (20 ml) and toluene (20 ml).. The mixture was stirred at ambient temperature for 1 hour and acetic acid (120 mg, 2 mmol) was added, followed by ether.. The insoluble materials were removed by filtration and the volatiles were removed by evaporation.. The residue was purified by column chromatography eluding with methylene chloride/acetonitrile/methanol (50/40/10 increasing to 50/30/20) to give 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-6-methoxy-7-(1-methylimidazol-2-ylmethoxy)quinoline (280 mg, 42%). 1H NMR Spectrum: (DMSOd6) 1.1 (s, 9H); 3.7 (s, 3H); 3.9 (s, 3H); 5.3 (s, 2H); 5.95 (d, 1H); 6.5 (d, 1H); 6.9 (s, 1H); 7.2 (s, 1H); 7.4-7.5 (m, 7H); 7.6 (s, 1H); 7.65-7.75 (m, 5H); 8.1 (d, 1); MS-ESI: 667 [MH]+.

The synthetic route of (1-Methyl-1H-imidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6809097; (2004); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-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 3012-80-4, HPLC of Formula: C9H8N2O

General procedure: Equimolar quantities of 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde and the respective aniline derivative were placed in microwave vial, and the reaction mixture was irradiated at 90?C during 4?min. After cooling to room temperature, the resulting residue was then purified by recrystallization in ethanol to give the pure Schiff base. N-(4-methoxyphenyl)-1-(1-methyl-1H-benzo[d]imidazol-2-yl)methanimine (L1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Boulebd, Houssem; Lahneche, Yousra Doria; Khodja, Imene Amine; Benslimane, Meriem; Belfaitah, Ali; Journal of Molecular Structure; vol. 1196; (2019); p. 58 – 65;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3097-21-0, These common heterocyclic compound, 3097-21-0, name is 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), arene (0.4 mmol,1 eq.), dichloroethane (2 mL), then 1 M hydrochloric acid (2 mL, 5 equiv). The solution wasallowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solution waswashed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.

The synthetic route of 3097-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A.; Chem; vol. 5; 2; (2019); p. 417 – 428;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10111-08-7, 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. 10111-08-7 name is Imidazole-2-carboxaldehyde, 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 imidazole-2-carboxaldehyde (lg), t-butyl bromoacetate (1 equivalent) andpotassium carbonate (1.5 equivalent) in 30 mL DMF was stirred at room temperature for 24 hours. The mixture was poured into water (50 mL) and then extracted with EtOAc two times (2x60mL). The combined organic layer was washed with water and then brine, followed by drying over anhydrous Na2S04. Evaporation of the solvent gave the product, which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Imidazole-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BIOTIUM, INC.; MAO, Fei; LEUNG, Wai-Yee; CHEUNG, Ching-Ying; HOOVER, Hye Eun; WO2011/68569; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-48-2, name is 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde, 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 870837-48-2, Formula: C10H7ClN2O

To a THF (13 mL) solution of 3-chloro-4-(1H-imidazol-1-yl)benzaldehyde (545 mg) dimethylphosphonoacetic acid methyl ester (513 muL) and lithium hydroxide monohydrate (133 mg) were added one by one, and the reaction solution was agitated overnight. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 442 mg of crude ester product. 2N sodium hydroxide solution (5.0 mL) was added to the reaction solution obtained by which dissolving the obtained ester product in THF (5.0 mL), and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0 C., 2N hydrochloric acid was added to the reaction solution, and the deposited precipitation was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 218 mg of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 8.08 (d, J=2.0 Hz, 1H), 7.93 (s, 1H), 7.82 (dd, J=2.0, 8.4 Hz, 1H), 7.61 (d, J=16 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.48 (s, 1H), 7.11 (s, 1H), 6.70 (d, J=16 Hz, 1H).

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

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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: C8H8N2O

The intermediate 1H-benzimidazole-2-methanol (1 g, 1 eq) and potassium permanganate (2.6 g. 1.5 eq) were added to dilute sodium hydroxide solution and heated at 100 ° C under reflux.After the reaction was completed, it was cooled to room temperature, the pH was adjusted to be acidic, and a brown solid was precipitated.Yield: 86percent.

The synthetic route of 4856-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Yu Jing; (20 pag.)CN110105286; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 2-(l-methyl-5-nitro-lH-imidazol-2-yl)-ethanol (1.25 mmol) and 2,4-di- chloro-l-fluorobenzene (1.45 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column:XBridge preparative C18 OBD column 19×150 mm, 5 urn; mobile phase A: water (10 mmol/L NH4HC03), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product- containing fractions were collected and then lyophilized to give 2-(2,4-dichloro-phenoxymethyl)- l-methyl-5-nitro-lH-imidazole. LC-MS: (ES, m/z) 302.00 (M+H)+; analysis: C, 43.78; H, 3.08; CI, 23.52; N, 13.81; O, 15.99.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methyl-1H-imidazole-4-carbaldehyde

To a solution of 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine (0.02 g, 0.051 mmol) in dichloroethane (0.5 mL) in a two dram vial was added 4-methyl-1H-imidazole-5-carbaldehyde (6 mg, 0.051 mmol), followed by a drop of acetic acid. The reaction mixture was shaken for 20 minutes at room temperature and then NaBH(OAc)3 was added (12 mg, 0.056 mmol). The reaction was stirred at room temperature overnight. The solvents were removed and the residue was purified by preparative HPLC (phenominex C18 column, 21×100 mm, 5 mu) using MeOH/H2O (with 0.1% TFA) to give 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-N-((4-methyl-1H-imidazol-5-yl)methyl)-2-phenylethanamine as a white solid (23.4 mg, 76% yield). LCMS: 3.6 min [M+1] 489.2 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) delta ppm 2.27 (s, 3H), 3.45-3.52 (m, 1H), 3.88-3.99 (m, 2H), 4.01-4.07 (m, 1H), 6.64 (d, J=7.09 Hz, 2H), 7.02 (d, J=8.56 Hz, 1H), 7.10 (t, J=7.46 Hz, 2H), 7.18 (t, J=7.46 Hz, 1H), 7.49 (d, J=7.58 Hz, 1H), 7.61 (d, J=9.54 Hz, 1H), 7.69 (s, 1H), 7.76 (dd, J=8.56, 2.45 Hz, 1H), 8.28 (s, 1H), 8.60 (d, J=1.96 Hz, 1H).

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 68282-53-1.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/161685; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24155-42-8, These common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, 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 2 2,6-Dichloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:1) 8.7 g of 4-bromomethyl-2,6-dichloroquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g of sodium hydroxide (0.75 mol) dissolved in 30 ml water, 0.5 g of benzyltrimethylammonium chloride and 100 ml of tetrahydrofuran are reacted as described in Example 1. Work up of the mixture results in an oil, which after treatment in boiling ether, is dissolved in 250 ml of ethyl acetate.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-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. HPLC of Formula: C11H12BrFN2

3.5 g of 6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole was dissolved in 20 ml of DMF.And add 5.1g of (BPin) 2, 0.62g of PCy3, 3.8g of KOAc and 0.3g of Pd(OAc)2, stir and heat to 100 C for 24h, stop heating and cool down to 6At 0 C, 50 ml of ethyl acetate was added, and the mixture was filtered.Add n-hexane to the oil obtained by concentration, stir and crystallize for 1 h at room temperature.Filtration gave 2.1 g of 4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-boronic acid pinacol ester as a pale yellow solid.

The synthetic route of 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem