Author: Jessica.F

Related Products of 71759-88-1,Some common heterocyclic compound, 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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 64 3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(1-methyl-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine A solution of 5-iodo-1-methyl-1H-imidazole (0.0217 g, 0.104 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxy-phenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.030 g, 0.070 mmol), potassium carbonate (0.0289 g, 0.209 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (2.84 mg, 0.00348 mmol) in previously degassed 4:1 dioxane:water (1.50 mL) was evacuated and charged with N2 (2*) and heated under microwave conditions [Biotage, 100 C., 30 min, high absorption]. The reaction mixture was partitioned between EtOAc and H2O and separated. The aqueous was back extracted with EtOAc (3*) and the combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo resulting in a crude brown oil. The crude was purified by chromatography on silica gel [ISCO Combiflash, 12 g cartridge, eluting with 100% DCM-8% MeOH in DCM]. This resulted in the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): delta=1.82 (d, J=7.3 Hz, 3H), 3.51 (s, 3H), 3.66 (br. s., 3H), 5.12 (q, J=7.1 Hz, 1H), 6.90 (dd, J=4.2, 9.0 Hz, 1H), 6.95 (s, 1H), 7.08 (dd, J=8.8, 8.8 Hz, 1H), 7.41 (d, J=1.0 Hz, 1H), 7.51 (s, 1H), 7.69 (s, 1H), 8.17 (d, J=2.0 Hz, 1H). MS (ES+): m/z 385.11, 387.07 (76/24) [MH+]. HPLC: tR=2.87 min (polar-5 min, ZQ3).

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

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); A1;,
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 10040-98-9 as follows. category: imidazoles-derivatives

General procedure: A methanolic sodium hydroxide solution (10%; 10.0 mL) was added drop-wise to a mixture of 1-(4-(1H-imidazol-1-yl)phenyl)ethanone(3) (10.0 mmol, 1.86 g), aromatic aldehyde (10.0 mmol) and methanol (50 mL) over a period of 30-40 min with continuous stirring at room temperature until completion of the reaction (as indicated by TLC). The reaction flask was kept in the freezer overnight. The obtained precipitates were filtered off and washed with a cold methanol-water mixture (1:10). Finally the product was purified by column chromatography using CHCl3:MeOH (97:3) as a solvent.

According to the analysis of related databases, 10040-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hussain, Tanvir; Zia-Ur-Rehman, Muhammad; Zaheer, Muhammad; Ashraf, Chouhdary Muhammad; Bolte, Michael; Journal of Chemical Research; vol. 40; 4; (2016); p. 199 – 204;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 tetrahydrofuran (20 mL) solution containing (1S,6R,9aR)-6-(4-chlorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione (685 mg) was cooled to -30 C. L-selectride (3.01 mL, 1.02 M tetrahydrofuran solution) was added dropwise, and stirring was continued for 2 hours at -20 C. to -30 C. 5 N sodium hydroxide solution (460 muL) was added to the reaction solution, and stirring was continued for 20 minutes at -20 C. to 0 C. Next, hydrogen peroxide solution (221 muL, 35% solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (237 mg) was added, and after stirring at room temperature for 20 minutes, ethyl acetate and brine were 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 (19.4 mL) and triphenylphosphonium bromide (796 mg) was added to the residue, and the resultant was heated under reflux for 2 hours. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (543 mg) and triethylamine (633 muL) were added, and stirring was continued for 12 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 organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate), and the title compound (640 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 480 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.48 (d, J=6.4 Hz, 3H), 2.29 (s, 3H), 3.51 (dd, J=11.2, 11.2 Hz, 1H), 3.74 (dd, J=12.0, 8.0 Hz, 1H), 3.83 (s, 3H), 3.99 (dd, J=11.2, 4.0 Hz, 1H), 4.18 (dd, J=12.4, 4.8 Hz, 1H), 4.41 (ddd, J=11.6, 4.0, 4.0 Hz, 1H), 4.50-4.56 (m, 1H), 4, 86 (dd, J=8.0, 4.4 Hz, 1H), 7.82 (s, 1H), 6.91 (s, 1H), 7.18 (d, J=8.8 Hz, 1H), 7.32-7.35 (m, 6H), 7.69 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, its application will become more common.

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

Reference of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 solution of t-BuOK (1 M in THF, 0.80ml) was added dropwise to a stirred mixture of B6 (R7 = p-SF5-Phenyl and R6 = carboethoxyl, 0.41 g) and A1(157 mg, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol-1 -yl) and R8 = H) in 10 ml_ of anhydrous THF at -70eC under nitrogen atmosphere. The reaction mixture was stirred between -709C and -30QC until starting material were consumed. The reaction was quenched with iced brine, and extracted with EtOAc. The organic phase was washed with aqueous NH4CI and brine, dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by a flash silica gel column and eluted with DCM/MeOH to give 0.38g B7 (R7 = p-SF5-Phenyl, R6 = carboethoxyl, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol- 1-yl)).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; XU, Ruo; CLADER, John, W.; WO2010/54064; (2010); 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H6N2S

STEP A 2-methylthio-1-methyl-imidazole 10 ml of a solution of 1.5% diazomethane in methylene chloride were added in 3 portions over 15 minutes at 0 C. to a solution of 1.14 g of 2-mercapto-1-methyl-imidazole in 5 ml of methylene chloride and after stirring at 0 C. for one hour, a second addition of 10 ml of the diazomethane in methylene chloride solution was made. The mixture was stirred at 20 C. for one hour and was then evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 1-1 methylene chloride-ethyl acetate mixture to obtain 1 g of 2-methylthio-1-methyl-imidazole.

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 60-56-0.

Reference:
Patent; Roussel Uclaf; US5663164; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

The synthetic route of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
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Imidazole | C3H4N2 – PubChem

Reference of 14741-71-0, 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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) containing triethylamine (0.50 mL) phenylisothiocyanate (1.30 g, 0.01 mol) was added. The reaction mixture was heated under reflux for 4 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Yellow crystals from ethanol; yield: 2.67 g (87%); m.p. 202 oC. IR, : 3057 (CH aromatic), 2980 (CH2), 1689 (CO), 1643 (C=N), 1632 (C=C).1H-NMR: : 5.90 (s, 2H, pyrimidine CH2), 7.26-7.38 (m, 9H, C6H4, C6H5). 13C NMR (DMSO): 54.2 (CH2), 120.3, 123.7, 124.1, 124.6, 124.9, 125.8, 129.3, 126.7, 127.2, 128.2 (C6H5, C6H4), 163.4 (CO), 173.6 (C=N), 180.3 (C=S); Anal. calcd for C16H11N3OS: C, 65.51; H, 3.78; N, 14.32; S, 10.93%. Found: C, 65.33; H, 4.02; N, 14.59; S, 11.27%. MS: m/z: (%) 293 (M+, 22%).

The synthetic route of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

116343-89-6, name is Methyl 1-phenyl-1H-imidazole-4-carboxylate, 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. Quality Control of Methyl 1-phenyl-1H-imidazole-4-carboxylate

LiOH.H2O (143 mg, 3.4 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid methyl ester (231 mg, 1.1 mmol) in a mixture of THF (3 mL), MeOH (1 mL), H2O (1 mL) and stirring was continued at ambient temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure. Cold water was then added and acidified it with 10% aqueous HCl, the solid was collected to afford 180 mg (83.7% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid.

The synthetic route of 116343-89-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

The 3 – (4 – methyl – 1H – imidazole -1 – yl) -5 – trifluoromethyl aniline free base (12.0 g, 50 mmol, purity 88.5%) dissolved in methanol (54 ml) and acetone (270 ml) in the mixed solvent,. 25 – 30 C lower, adding concentrated hydrochloric acid (5.43 g, 55 mmol). The temperature slowly, about 15 – 20 C precipitated solid, lowering the temperature to – 10 – – 5 C stirring 2 hours, filtering, and washing the filter cake with cold acetone, 80 C and 10 – 20 mm Hg pressure drying to constant weight, to obtain the hydrochloride of crystalline form A solid 11 g, moisture 0.19%, purity 99.69%. Its X-ray powder diffraction pattern as shown in Figure 1; its heats analysis chart as shown in Figure 2.

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

Reference:
Patent; Jiangsu Chuangnuo Pharmaceutical Co., Ltd.; Anlite (Shanghai) Pharmaceutical Technology Co., Ltd.; Shanghai Chuangnuo Pharmaceutical Group Co., Ltd.; Niu Deliang; Ma Bojun; Zhu Zhanqun; Wan Qiang; (10 pag.)CN108530364; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, molecular formula is C8H6N2O2, 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: C8H6N2O2

General procedure: A solution of 6-chloronicotinic acid (2.0 g, 0.012 mole) in DMF (5 mL) was added to a suspension of sodium hydride (0.76 g, 0.015 mole) in DMF (3 mL) under N2 at 25 C and stirred for 1 hour. Methyl iodide (1.5 mL, 0.025 mole) was added at RT and warmed to 50 C for 2 hours. Reaction mixture was cooled to RT, quenched in to ice cold water (50 mL) and extracted with ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL), dried over Na2SC>4 and concentrated under vacuum to obtain methyl 6-chloronicotinate. Yield: 1.6 g; Mass (m/z): 172.0, 174.0 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 46006-36-4, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); A1;,
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Imidazole | C3H4N2 – PubChem