Author: Jessica.F

These common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-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. Application In Synthesis of 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole

7 g of 1-(4-bromophenyl)-2-phenylbenzimidazole (0.02 mol) was added to 150 ml of THF, and the temperature was lowered to -78 C, and 12 ml (2.5 M/L, 0.03 mol) was added dropwise at -78 C. n-BuLi, keep warm for 30 minutes, add 4.26g (0.041mol) of trimethyl borate, after 2 hours of reaction, the reaction is completed, add 50ml of water to the reaction solution, stir for 20 minutes, add hydrochloric acid to adjust the pH to acidity, stir 30 The reaction solution was extracted three times with ethyl acetate. The organic layer was combined and washed with water, and then the organic phase was separated and evaporated to dryness. The solid was digested twice with petroleum ether and filtered to give 2 g of white solid intermediate A, yield 60%.

The synthetic route of 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Qian Chao; Xu Jun; Wang Dening; (108 pag.)CN104987309; (2019); B;,
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Imidazole | C3H4N2 – PubChem

137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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: 137049-00-4

General procedure: 2-Aminoethyl amine (1 equiv.) and 2-trifluormethyl-4-fluoro benzonitrile(1 equiv.) were dissolved under argon in dry MeCN, followedby addition of Et3N (1.5 equiv). The resulting reaction mixture wasstirred at 50 C for 4 h. After cooling to room temperature water andCH2Cl2 were added, followed by thorough extraction. The combinedorganic layer was dried over Na2SO4, filtered and concentrated underreduced pressure to afford desired 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile. 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile (160 mg, 0.69 mmol) was dissolved in a flame-dried roundbottomedflask in CH2Cl2 (20 mL) under argon and diisopropylethylamine (0.37 mL, 2.09 mmol) was added. After stirring at room temperaturefor 5 min a solution of the corresponding aryl- or hetarylsulfonylchloride (0.69 mmol) in dry CH2Cl2 (5 mL) was added, andthe resulting reaction mixture was stirred at room temperature for20 h¡¤H2O and CH2Cl2 were added, followed by thorough extraction. Thecombined organic layer was dried over Na2SO4, filtered, concentratedunder reduced pressure and purified via column chromatography(heptane/EtOAc, gradient 10:0 to 1:1) to afford desired N-(2-{[4-cyano-3-(trifluormethyl)phenyl]amino}-ethyl)-aryl-/hetaryl sulfonamide 9i-z.

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 693-98-1,Some common heterocyclic compound, 693-98-1, name is 2-Methyl-1H-imidazole, molecular formula is C4H6N2, 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 the reaction vessel containing benzimidazole or imidazole (1mmol), alkyl halide (1mmol), 50% NaOH (0.5mL) and anionic surfactant sodium dodecyl sulfate (5mol%) was added and the reaction mixture was vigorously stirred at room temperature or 60C. After the completion of reaction (TLC) followed by standard workup using ethyl acetate as extracting solvent the crude product was purified over silica-gel (60-120 mesh) using ethyl acetate-hexane (3:7) as eluent to afford pure products. Identities of the products were judged by the comparison of melting point, IR data, 1H NMR, 13C NMR and HRMS analyses.

The synthetic route of 693-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chakraborty, Ankita; Debnath, Sudipto; Ghosh, Tanmoy; Maiti, Dilip K.; Majumdar, Swapan; Tetrahedron; vol. 74; 40; (2018); p. 5932 – 5941;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1739-84-0, name is 1,2-Dimethyl-1H-imidazole, 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 1739-84-0, SDS of cas: 1739-84-0

General procedure: Quaternization of 1,2-dimethylimidazole withalkyl halides was performed in acetonitrile (50% solution)at the boiling point of the solvent and an equimolarratio of the starting reagents for 48 h. The solvent was then removed, and lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30% solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. The desired product precipitated from water into the lower liquid phase. The upper aqueous layer was decanted, methylene chloride (equal volume) was added to the lower layer, and the resulting solution was washed again with distilled water till negative reaction to Cl- with AgNO3. The ionic liquids were dried by azeotropic distillation of absolute methylene chloride, then the traces of the organic solvent were removed in vacuum by heating (3 h at 100C).

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

Reference:
Article; Krasovskiy; Chernikova; Glukhov; Kapustin; Koroteev; Russian Journal of Physical Chemistry; vol. 92; 12; (2018); p. 2379 – 2385; Zh. Fiz. Khim.; vol. 92; 12; (2018); p. 1851 – 1858,8;,
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Imidazole | C3H4N2 – PubChem

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. 623577-60-6, name is 4-Bromo-1-isopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H9BrN2

To the solution of compound 113-la (50 mg, 0.26 mmol, 1 eq) in dioxane (2 mL) was added compound 113-1 (125 mg, 0.32 mmol, 1.2 eq), Pd(PPh3)4 (31 mg, 26.5 umol, 0.1 eq), Cs2C03 (172 mg, 0.53mol, 2 eq) and H20 (0.4 mL). The mixture was stirred at 100 C for 16 hr. The reaction was monitored by LCMS. LCMS showed that the starting material was consumed and the desired MS was observed. The reaction solution was filtered. The residue was purified by HPLC to give Compound 113 (9.07 mg, 23.61 umol, 8.9% yield). LCMS (ESI): RT = 0.649 min, mass calcd. for C19H23N9O 376.19, m/z found 377.0 [M+H]+, Ti NMR (400MHz, CDCI3) delta 8.71 (br , 1H), 7.89 (d, J= 2.5 Hz, 1H), 7.57 – 7.51 (m, 2H), 7.36 (d, J = 1.0 Hz, 1H), 6.68 (d, J = 8.8 Hz, 1H), 4.52 (q, J = 5.4 Hz, 1H), 4.41 – 4.30 (m, 1H), 3.44 (br , 1H), 2.61 (d, J=5.5 Hz, 3H), 2.10 – 2.02 (m, 2H), 1.84 – 1.75 (m, 2H), 1.69 – 1.60 (m, 1H), 1.51 (d, J = 6.8 Hz, 6H), 1.46 – 1.27 (m, 5H).

The synthetic route of 623577-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, A new synthetic method of this compound is introduced below., Computed Properties of C8H6N2O2

Example 180N-((ls,4s)-4-(5-Fluoro-2-(4′-((4-(2-hydroxyethyl)-l,4-diazepan-l-yl)methyl)-2′-(((S)-3- methylmorpholinoJmethylJbiphenyl-S-yloxyJnicotinamidoJcyclohexylJ-lH- benzo [d] imidazole-4-carboxamide To a solution of N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(4′-((4-(2-hydroxyethyl)-l,4- diazepan- 1 -yl)methyl)-2′-(((S)-3 -methylmorpholino)methyl)biphenyl-3 -yloxy Nicotinamide (200 mg, 0.24 mmol) in dry DMF (5 mL) under nitrogen was added DIPEA (0.161 mL, 0.97 mmol) at RT. The solution was stirred until homogeneous. To this solution was added dropwise a solution of lH-benzo[d]imidazole-4-carboxylic acid (39.5 mg, 0.24 mmol) and l,l’-carbonyldiimidazole (39.5 mg, 0.24 mmol) in dry DMF (5 mL) under nitrogen which had been allowed to stir at 40 0C for 1 hour. The reaction mixture was allowed to stir at 50 0C overnight. The mixture was evaporated to dryness and the residue dissolved in DCM (100 ml) and washed with saturated NaHCC^aq), brine, dried (MgSC^) and evaporated to give a yellow oil. The crude product was purified by preparative HPLC using a 95-5% gradient of aqueous 0.2% ammonia in methanol as eluent to give the the title compound as a white solid. Yield: 22 mg1H NMR (W MHz, CDCl3) delta 8.12 – 8.06 (m, 2H), 7.94 – 7.82 (m, 2H), 7.70 (d, J= 7.9 Hz, IH), 7.43 (d, J= 7.9 Hz, IH), 7.38 – 7.31 (m, 2H), 7.24 – 7.10 (m, 5H), 7.07 (d, J= 7.9 Hz, IH), 4.25 – 4.18 (m, IH), 4.16 – 4.09 (m, IH), 3.82 (d, J= 13.9 Hz, IH), 3.64 – 3.58 (m, 5H), 3.49 – 3.43 (m, IH), 3.40 – 3.31 (m, IH) 3.03 – 2.93 (m, 2H), 2.81 – 2.73 (m, 5H) 2.72 – 2.62 (m, 7H), 2.39 – 2.31 (m, IH), 2.12 – 2.03 (m, IH), 1.98 – 1.74 (m, 10H), 0.66 (d, J= 6.2 Hz, 3H). MS: [M+H]+=819 (calc=819) (MultiMode+)

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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; [240] Preparation of N-r3-f4-methylimidazol- l-ylV5-trifluoromethyl-phenyll-4-(4-pyridin-3-yl-Pyrimidin-2-ylaminos)-benzamide; EPO [241] 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid prepared in Preparation 19(242mg, 0.83mmol) and 3-(4-methyl-imidazol- l-yl)-5-trifluoromethyl-phenylamine prepared in Preparation 30 (200mg, 0.83mmol), N,N-dimethyl formamide (10ml), and diethylcyano phosphate ( 0.245ml, 1.658mmol) were added to a reaction vessel, and cooled to 100C. Triethylamine (0.231ml, 1.658mmol) was added thereto. After 30 min, the mixture was mixed at 600C for 15 hr. The mixture was cooled to RT, and an organic layer was obtained with the solution of ethyl acetate and sodium bi carbonate, concentrated under vacuum, and subjected to column chromatography (5: 1/CHC1 :MeOH) to give the titled compound as pale yellow solid.[242] 1H-NMR (DMSO-d , delta)= 2.20 (s,3H), 7.39 (s,lH), 7.56 (d,2H), 8.03 (m,5H), 8.17(s,lH), 8.21 (d,lH), 8.32 (s,lH), 8.49 (d,2H), 8.63 (d,lH), 8.72 (d,lH), 9.36 (s,lH), 10.15 (s, IH); 10.48 (s,lH)

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

Reference:
Patent; IL-YANG PHARM. CO., LTD.; WO2007/18325; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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 suspension of sodium hydride (2mmol, 2eq) in THF (5mL) was treated with a solution of 2-(1H-imidazol-1-yl)ethanol (1mmol, 1eq) in THF (3mL) at 0C. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1h. The mixture was cooled to 0C before addition of 2,4-dichlorobenzyl bromide (1, 1.5mmol, 1.5eq). The resulting mixture was stirred under reflux for 3h. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl (5mL). The aqueous phase was extracted with ethyl acetate (15mL, three times), the organic phase was washed with water (10mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography (SiO2, MeOH/ethyl acetate) afforded 2 as an oil in 65% yield. IR (film): numax: 3109, 2868, 1898, 1589, 1505, 1469, 1075, 813, 737cm-1. 1H NMR (400MHz, CDCl3): delta 7.55 (bs, 1H), 7.37 (s, 1H), 7.24-7.23 (m, 2H), 7.07 (bs, 1H), 6.98 (s, 1H), 4.56 (s, 2H), 4.17 (t, 2H, J=5.1Hz), 3.79 (t, 2H, J=5.1Hz) ppm. 13C NMR (100MHz, CDCl3): delta 137.5, 133.9, 133.88, 133.3, 129.6, 129.4, 129.1, 127.0, 119.4, 70.0, 69.6, 47.0ppm. ESI-TOF-HRMS: m/z calcd for (M+H) C12H12N2Cl2O 271.0405 found 271.0416.

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

Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Chambon, Marc; Bron, Sylvian; Pilotte, Luc; Colau, Didier; Van Den Eynde, Benoit J.; Turcatti, Gerardo; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 284 – 301;,
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Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 500 ml, three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, ethyl 4-amino-3-phenylbutanoate hydrochloride x42 (synthesized as described in patent application EP1265862, 6.2 g, 38 mmol), 1-trityl-1 H- imidazole-4-carbaldehyde x43 (Dolensky B., Kirk K.L., Collect. Czech. Chem. Commun. (2002), 67, 1335-1344; 8.2 g, 36.1 mmol) and MeOH (150 ml) are stirred at room temperature. Triethylamine (3.9 ml, 41.85 mmol) and NaBH4 (1.06 g, 41.8 mmol) are added by portions. The mixture is stirred at 45 0C for 3 h, then at room temperature overnight. CH2CI2 (300 ml) and water (300 ml) are added, the aqueous phase is extracted with CH2CI2 (2 x 200 ml). The combined organic phases are washed with a saturated solution of NH4CI (2 x 150 ml), dried, filtered and concentrated in vacuo. The crude product is recrystallized from AcOEt to afford 4-phenyl-1 -[(1 -trityl-1 H-imidazol-4- yl)methyl]pyrrolidin-2-one x44.Yield: 36 %.LC-MS (MH+): 484.

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-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 23328-88-3, These common heterocyclic compound, 23328-88-3, name is 2-Bromo-4-methyl-1H-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.

Step 1: 2-(2-bromo-4-methyl-1H-imidazol-1-yl)-6-methoxy-3-nitropyridine To a mixture of 2-chloro-3-nitro-6-methoxypyridine (9.43 g, 50 mmol) and 2-bromo-4-methylimidazole (9.66 g, 60 mmol) in 300 mL of DMF was added freshly powdered KOH (3.36 g, 60 mmol) at 0 C. The resulting mixture was stirred at RT for 4 h. Solvent was removed by rotavap and the residue was washed with water and extracted with ethyl acetate (3*). Standard work-up followed by column chromatography using 30-50% ethyl acetate in hexane as eluent provided the product (13.82 g, 88% yield). MS (ESI) 313.0 [M+H]+

Statistics shows that 2-Bromo-4-methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 23328-88-3.

Reference:
Patent; WYETH; US2010/120762; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem