Month: May 2021

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. 1038408-36-4, name is 6-Bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Product Details of 1038408-36-4

Under nitrogen protection, TCHP (460 mg) and Pd(Oac)2 (230 mg) were added into the mixture of 228 6-bromo-2-methyl-1-isopropyl-1H-benzo[d]imidazole (2.30 g, 9.10 mmol), 27 bis(pinacolato)diboron (3.50 g, 13.6 mmol) and 28 potassium acetate (2.70 g, 27.3 mmol) in anhydrous 29 DMSO (25 mL), and the reaction was reacted under nitrogen protection at 100 C. for 2 hrs. After cooling to room temperature, the reaction was quenched by adding 48 water, extracted with ethyl acetate (100 mL¡Á3), the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=2:1), to afford 1.60 g of a brown-yellow solid, yield was 58.6%. LC-MS(APCI): m/z=301.2 (M+1).

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; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33469-36-2,Some common heterocyclic compound, 33469-36-2, name is 2-Phenyl-4-(trifluoromethyl)-1H-imidazole, molecular formula is C10H7F3N2, 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: Avessel containing 2-(2,6-dimethoxyphenyl)-4-(trifluoromethyl)-1H-imidazole (A) (3.734 g, 13.7 mmol) was chargedwith 18 mL of 3.75 N sodium hydroxide.The vessel was equipped with a condenser and heated in a 100 C oil bathfor 22 h. The mixture was cooled,diluted with 20 mL of water and washed once with 20 mL of ethyl acetate. The pH of the aqueous part was adjusted toca. 3 with 3 M HCl. The turbid solutionwas placed in a refrigerator for 5 h before collecting a solidprecipitate. The filtrate wasrefrigerated overnight to yield a smaller second crop for a combined recoveryof 3.202 g (94%) of 2-(2,6-dimethoxyphenyl)-1H-imidazole-4-carboxylic acid (B) as a pale pink solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Phenyl-4-(trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Article; Hershberger, Paul M.; Hedrick, Michael P.; Peddibhotla, Satyamaheshwar; Mangravita-Novo, Arianna; Gosalia, Palak; Li, Yujie; Gray, Wilson; Vicchiarelli, Michael; Smith, Layton H.; Chung, Thomas D.Y.; Thomas, James B.; Caron, Marc G.; Pinkerton, Anthony B.; Barak, Lawrence S.; Roth, Gregory P.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 262 – 267;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 31250-80-3, 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. 31250-80-3, name is 1-Benzyl-2,4,5-tribromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

The synthetic route of 1-Benzyl-2,4,5-tribromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
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. 78597-27-0, name is 6-Iodo-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Iodo-1H-benzo[d]imidazole

Preparation 23 Preparation of a Mixture OF 6-IODO-1- [3- (TETRAHYDRO-PYRAN-2-YLOXY)-PROPYL]-LH- benzoimidazole and 5-IODO-1- [3- (TETRAHYDRO-PYRAN-2-YLOXY)-PROPYL]-LH- benzoimidazole Stir 5-IODO-LH-BENZOIMIDAZOLE (U. S. S. R. pat. 1616911,30 Dec. 1990; 2.0 g, 8.2 mmol), 2- (2-bromoethoxy) tetrahydro-2H-pyran (4.0 mL, 26.5 mmol), sodium hydride (0.78 g, 32.8 mmol) in DMF (20 mL) at room temperature for 2 h. Extract the product with 3: 1 CHLOROFORM/ISOPROPYL alcohol and wash with saturated sodium chloride. Dry the organic phase over sodium sulfate and filter to give a dark yellow oil. Purify by silica gel flash chromatography eluting with dichloromethane to 10% THF/90% dichloromethane to afford a light yellow oil as a mixture of the two titled compounds (2.59 g, 83%). MS (electrospray, m/z) 387.1 (M+1).

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; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3718-04-5, A common heterocyclic compound, 3718-04-5, name is 5-Vinyl-1H-imidazole, molecular formula is C5H6N2, 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 35 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-( 1 -propyl- lH-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (400 mg, 4.25 mmol) was dissolved in THF (2 mL) and the solution was cooled to 0 C. The reaction vial was charged with 60% sodium hydride in mineral oil (170 mg, 4.25 mmol) and the reaction mixture stirred for 10 min at 0 C. To the mixture was added 1-iodopropane (0.415 mL, 4.25 mmol) and the reaction was stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and diluted with dichloromethane (25 mL). The organic phases were combined, passed through a phase separator and concentrated to afford the crude product. The crude material was purified by column chromatography (1-10% dichloromethane/methanol) to afford a mixture of l-propyl-4-vinyl-lH-imidazole and l-propyl-5-vinyl-lH-imidazole (511 mg, 3.72: 1). l-propyl-4-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.83 – 0.91 (m, 3 H), 1.66 – 1.82 (m, 2 H), 3.74 – 3.90 (m, 2 H), 5.11 (dd, J=11.12, 1.52 Hz, 1 H), 5.73 – 5.87 (m, 1 H), 6.52 (dd, J=17.18, 11.12 Hz, 1 H), 6.80 (s, 1 H), 7.58 (s, 1 H). l-propyl-5-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.78 – 0.93 (m, 3 H), 1.63 – 1.82 (m, 2 H), 3.76 – 3.90 (m, 2 H), 5.22 (d, J=11.12 Hz, 1 H), 5.57 (d, J=17.18 Hz, 1 H), 6.41 (dd, J=17.43, 11.37 Hz, 1 H), 7.17 (s, 1 H), 7.63 (s, 1 H). To a microwave vial, l-(4-bromophenyl)-2-(4-fluorophenyl)-6-methoxy-l- methyl- 1, 2,3 ,4-tetrahydroisoquinoline (0.13 g, 0.305 mmol) was dissolved in DMF (2 mL) and triethylamine (213 mu^, 1.525 mmol). To the solution was added a mixture of 1 -propyl -4-vinyl- lH-imidazole and l-propyl-5 -vinyl- lH-imidazole (125 mg, 0.915 mmol) and Pd(PPh3)2Cl2 (0.032 g, 0.046 mmol). The system was flushed with nitrogen and heated at 150 C for 1 h under microwave radiation. The mixture was cooled to room temperature and quenched with saturated ammonium chloride. The reaction mixture was extracted with dichloromethane (3 x), the organic layers were combined, passed through a phase separator, and concentrated to give crude material. The crude material was purified by silica gel chromatography (0-75% ethyl acetate/heptanes) to afford mixture of two isomers (141 mg, 0.293 mmol, 96% yield). LC MS (m/z, MH+): 482.1.

The synthetic route of 3718-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3718-04-5, 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 3718-04-5 as follows.

Example 35 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-( 1 -propyl- lH-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (400 mg, 4.25 mmol) was dissolved in THF (2 mL) and the solution was cooled to 0 C. The reaction vial was charged with 60% sodium hydride in mineral oil (170 mg, 4.25 mmol) and the reaction mixture stirred for 10 min at 0 C. To the mixture was added 1-iodopropane (0.415 mL, 4.25 mmol) and the reaction was stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and diluted with dichloromethane (25 mL). The organic phases were combined, passed through a phase separator and concentrated to afford the crude product. The crude material was purified by column chromatography (1-10% dichloromethane/methanol) to afford a mixture of l-propyl-4-vinyl-lH-imidazole and l-propyl-5-vinyl-lH-imidazole (511 mg, 3.72: 1). l-propyl-4-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.83 – 0.91 (m, 3 H), 1.66 – 1.82 (m, 2 H), 3.74 – 3.90 (m, 2 H), 5.11 (dd, J=11.12, 1.52 Hz, 1 H), 5.73 – 5.87 (m, 1 H), 6.52 (dd, J=17.18, 11.12 Hz, 1 H), 6.80 (s, 1 H), 7.58 (s, 1 H). l-propyl-5-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.78 – 0.93 (m, 3 H), 1.63 – 1.82 (m, 2 H), 3.76 – 3.90 (m, 2 H), 5.22 (d, J=11.12 Hz, 1 H), 5.57 (d, J=17.18 Hz, 1 H), 6.41 (dd, J=17.43, 11.37 Hz, 1 H), 7.17 (s, 1 H), 7.63 (s, 1 H). To a microwave vial, l-(4-bromophenyl)-2-(4-fluorophenyl)-6-methoxy-l- methyl- 1, 2,3 ,4-tetrahydroisoquinoline (0.13 g, 0.305 mmol) was dissolved in DMF (2 mL) and triethylamine (213 mu^, 1.525 mmol). To the solution was added a mixture of 1 -propyl -4-vinyl- lH-imidazole and l-propyl-5 -vinyl- lH-imidazole (125 mg, 0.915 mmol) and Pd(PPh3)2Cl2 (0.032 g, 0.046 mmol). The system was flushed with nitrogen and heated at 150 C for 1 h under microwave radiation. The mixture was cooled to room temperature and quenched with saturated ammonium chloride. The reaction mixture was extracted with dichloromethane (3 x), the organic layers were combined, passed through a phase separator, and concentrated to give crude material. The crude material was purified by silica gel chromatography (0-75% ethyl acetate/heptanes) to afford mixture of two isomers (141 mg, 0.293 mmol, 96% yield). LC MS (m/z, MH+): 482.1. A mixture of (E)-2-(4-fluorophenyl)-6-methoxy-l-methyl-l-(4-(2-(l-propyl- lH-imidazol-4-yl)vinyl)phenyl)- 1,2,3 ,4-tetrahydroisoquinoline and (E)-2-(4-fluorophenyl)-6- methoxy- 1 -methyl- 1 -(4-(2-( 1 -propyl- 1 H-imidazol-5-yl)vinyl)phenyl)- 1 ,2,3 ,4- tetrahydroisoquinoline (0.141 g, 0.293 mmol) was dissolved in dichloromethane (2.93 mL) and cooled to 0 C. Ethanethiol (404 mu , 5.46 mmol) was added followed by aluminum chloride (293 mg, 2.196 mmol). The reaction was warmed to room temperature and stirred for 3 h. The reaction was quenched with water and brought to pH 6 with saturated sodium bicarbonate. The aqueous layer was extracted thrice with dichloromethane. The organic layers were combined, passed through a phase separator, and concentrated. The crude material was purified by silica gel chromatography (0-75% ethyl acetate/heptanes) to afford a mixture of the two isomer products (69 mg). This mixture was urified via SFC (25% methanol with 10 mM ammonium hydroxide in carbon dioxide) to provide one single isomer (E)-2-(4-fluorophenyl)- 1 -methyl- l-(4-(2-(l -propyl- lH-imidazol-4-yl)vinyl)phenyl)-l,2,3,4-tetrahydroisoquinolin-6-ol as a white solid (17 mg, 12% yield). LC MS (m/z, MH+): 468.2. NMR (400 MHz, METHANOL-^) delta 0.86 (t, J=7.33 Hz, 3 H), 1.56 (s, 3 H), 1.78 (sxt, J=7.28 Hz, 2 H), 2.73 – 2.84 (m, 1 H), 2.93 – 3.05 (m, 1 H), 3.09 – 3.17 (m, 1 H), 3.31 – 3.40 (m, 1 H), 3.96 (t, J=7.07 Hz, 2 H), 5.39 (s, 1 H), 6.37 – 6.44 (m, 1 H), 6.45 – 6.61 (m, 5 H), 6.62 – 6.70 (m, 2 H), 6.85 – 6.95 (m, 1 H), 7.00 – 7.11 (m, 3 H), 7.27 (d, J=8.08 Hz, 2 H).

According to the analysis of related databases, 3718-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50591-22-5, These common heterocyclic compound, 50591-22-5, name is 1-Methyl-1H-benzo[d]imidazol-5-ol, 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 98 NaH (204 mg, 8.49 mmol) in 47 DMF (5 mL) was added 203 1-methyl-1H-benzo[d]imidazol-5-ol (420 mg, 2.83 mmol) at 28 C. After being stirred for 5 minutes, 41 ethyl 2-bromoacetate (568 mg, 3.4 mmol) was added and the resulting mixture stirred for a further 16 h under the reaction was complete by TLC. The mixture was treated with 43 water (50 mL) and extracted with ethyl acetate (2¡Á20 mL). The water layer was treated with 2N 44 HCl until pH 3 and extracted with ethyl acetate (2¡Á20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 205 product (160 mg, 24.1%) as white solid which was used in next step without further purification. LCMS (m/z): 207.1 (M+1).

The synthetic route of 50591-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Duncan, Kenneth W.; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Munchhof, Michael John; Jin, Lei; (118 pag.)US2019/83482; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2080-75-3, 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. 2080-75-3, name is 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5.2 5-Methoxy-6-nitro-1H-benzo[d]imidazol-2(3H)-one (9) A solution of 17.5% fuming nitric acid (12.5 mL, 48.9 mmol) was slowly added to 5-methoxy-1H-benzo[d]imidazol-2(3H)-one (0.25 g, 1.5 mmol) at 0 C, and the reaction was stirred for 1 h at 0 C, and at 20 C for 3 h. The reaction mixture was cooled to 0 C and neutralised with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (2 * 50 mL), washed with water, dried, and concentrated to give 9 (113 mg, 36%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) delta = 11.21 (br s, 1H), 10.81 (br s, 1H), 7.47 (s, 1H), 6.80 (s, 1H), 3.89 (s, 3H); MS ES+ve m/z 210 (M+H)+, 251 (M+H+MeCN)+.

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, 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
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 89088-69-7 as follows. Computed Properties of C4H8ClN3

Intermediate 22; 6-Chloro- 1 -methyl-iV-( 1 -methyl- lH-imidazol-4-yl)- lH-pyrazolo[3 ,4-Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 66247-84-5, These common heterocyclic compound, 66247-84-5, name is (1H-Imidazol-4-yl)methanamine hydrochloride, 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 1 N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride A suspension of indole-3-carboxylic acid (0.592 g) and thionyl chloride (0.6 ml) in 1,2-dichloroethane (50 ml) was stirred at room temperature for 60h under nitrogen. The suspension was evaporated in vacuo and further 1,2-dichloroethane (50 ml) was added. The suspension was re-evaporated to give a solid (0.6 g) which was dissolved in acetonitrile (25 ml) and triethylamine (5 ml), and added to a stirred suspension of imidazole-4-methanamine dihydrochloride (0.684 g) and triethylamine (5 ml) in acetonitrile (25 ml) at -5¡ã under nitrogen. The reaction was stirred for 1h while warming to room temperature and then heated at reflux for 20h. The mixture was evaporated in vacuo, dissolved in methanol (20 ml) and partitioned between hydrochloric acid (0.2N; 2*200 ml) and dichloromethane (2*100 ml). The combined aqueous layers were basified with saturated potassium carbonate and extracted with chloroform (3*150 ml). The combined chloroform layers were dried and evaporated in vacuo to give a semi-solid which was triturated with ether to give a solid (0.24 g). This was adsorbed onto silica and purified by FCC eluding with System A (83.5:151.5) to give a solid (ca. 50 mg) which was dissolved in methanol (3 ml) and acidified with ethanolic hydrogen chloride. Dry ether (20 ml) was added until the solution turned cloudy, precipitating the title compound (26 mg), m.p. 225¡ã-229¡ã (decomp.). Analysis Found: C,55.1; H,4.7; N,19.5; C13 H12 N4 O. HCl. 0.38H2 O requires C,55.1; H,4.5; N,19.5percent

Statistics shows that (1H-Imidazol-4-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 66247-84-5.

Reference:
Patent; Glaxo Group Limited; US5026722; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem