Tag: M.W=100-200

54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Tri-tert-butylphosphine (4.4 mL of 1.0 M in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (22.8 g, 238 mmol)A solution of 2-bromo-1H-benzimidazole (36.0 g, 183 mmol) and p-methoxybromobenzene (35.0 g, 187 mmol) in degassed toluene (1 L) was added and the mixture was heated under reflux 2 hour.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc.The filtrate was diluted with water and extracted with toluene and the organic phases were combined and evaporated in vacuo.The residue was filtered through silica gel and recrystallized.Compound a (44.2 g, yield 80percent) was obtained.

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (35 pag.)CN108218787; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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. 2302-25-2

Step 3: 4-Bromo-1 H-imidazole (Aldrich) (500 mg, 3.40 mmol) is charged in a round-bottom flask and dissolved in THF (10 ml_). 2-Bromoacetophenone (Aldrich) (1 .35 g, 6.80 mmol, 2.00 eq) and potassium carbonate (940 mg, 6.80 mmol, 2.00 eq) are added. The reaction mixture is stirred for 16 h at RT, diluted with EtOAc and washed with water. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (100 % hexanes to 50 % EtOAc in hexanes) to provide intermediate 4044C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2302-25-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); 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 3314-30-5 as follows. 3314-30-5

To a mixture of X4-011-1 (2 g, 12.4 mmol) and 1H-benzo[d]imidazole-2- carbaldehyde (2.72 g, 18.6 mmol) in MeOH (60 ml) was added a solution of NaOH (992 mg, 24.8 mmol) in H20 (4 ml) at 0 ¡ãC and the mixture was stirred at room temperature for 3 h. The solution was adjusted pH to 8 with 35percent HC1 aq., dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography to give X4-011-2 (2.7 g, 75.2 percent yield) as a yellow solid. LCMS (Agilent LCMS 1200-6110, Column: Waters XBridge C18 (50 mm*4.6 mm*3.5 jim); Column Temperature: 40 ¡ãC; Flow Rate: 2.0 mL/min; Mobile Phase: from 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] to 0percent [0.05percent aq. TFA] and 100percent [CH3CN + 0.05 percent TFA] in 1.6 mm, then under this condition for 1.4 mm, finally changed to 95percent [0.05percent aq. TFA] and 5percent [CH3CN + 0.05percent TFA] in 0.05 mm and under this condition for 0.7 mi. Purity: 99percent; Rt = 1.32 mm; MS Calcd.: 289.1; MS Found: 290.1 [M+H].

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, Adding some certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8.

To 100 mg (0.36 mmol) of (S)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-6-methyl-3,6-dihydro- 2H-1,3,4-oxadiazin-2-one (Intermediate 75) and 73 mg of 4-trifluoromethyl imidazole (0.54 mmol) dissolved in 2 mL of DMF was added 235 mg of powdered Cs2C03 (0.72 mmol) and the mixture was heated at 80 Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2.

Add tetrakis (triphenylphosphine) palladium (0) (500 mg) to a degassed suspension of H-IMIDAZOLE (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4- (2- ISOPROPOXYPHENYL)-1H-IMIDAZOLE (5.01 g, 73%) which is used without further purification in the next step.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19184; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-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. 872-82-2

Preparation 32 4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-imidazole A solution of 2-(1H-imidazol-4-yl)ethanol (1.24 g, 11.1 mmol) in DMF (10 mL) was treated with imidazole (1.51 g, 22.1 mmol) and TBDPSCl (3.12 mL, 12.2 mmol) and the mixture was stirred at RT for 2 h. The mixture was then poured onto H2O and extracted with AcOEt. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/heptane 0:100 to 100:0) gave the title compound (1.6 g). UPLC-MS: MS 351.2 (M+H+); UPLC rt 1.02 min.

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 872-82-2.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, molecular formula is C8H7N3O2, 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. 1792-40-1

[0182] (1) Benzoyl chloride (32.5 ml) was added dropwise to a mixture of 2-methyl-5-nitrobenzimidazole (12.5 g) and TEA (38.8 ml) in Diglyme (63 ml) at room temperature. The reaction mixture was stirred at 100[deg.] C. for 1 hour. Water was added to the reaction mixture cooled to room temperature and the whole was stirred for 45 minutes. The reaction mixture was extracted with chloroform, the organic layer was washed with water and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained crude crystals were recrystallized from chloroform-n-hexane to obtain 2-(1-benzoyl-1H-5-nitrobenzimidazol-2-yl)-1-phenylvinyl benzoate (29.7 g, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1792-40-1, its application will become more common.

Reference:
Patent; Hirano, Masaaki; Kawaminami, Eiji; Toyoshima, Akira; Moritomo, Hiroyuki; Seki, Norio; Wakayama, Ryutaro; Okada, Minoru; Kusayama, Toshiyuki; US2003/191164; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-22-5, name is 6-Aminobenzimidazole, 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 934-22-5, 934-22-5

General procedure: [0205] A solution of benzimidazol-5-amine (1 eq.) in DMF (5 ml) was treated with K2CO3 (2.2 eq.) and the respectivealkylhalide (2.2 eq.) and stirred at room temperature for 24 h. The mixture was diluted with water and extracted by meansof ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4, evaporated and the residue waspurified by flash chromatography on silica using a CHCl3/MeOH gradient; Example 20 N,N-Bis((4-methylbenzyl)-1H-benzo[d]imidazol-5-amine The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 4-methylbenzylbromide (407 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.109 g (32.0%); MS m/z: 342.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): delta 2.23 (s, 6H); 4.57 (s, 4H); 6.66 (br s, 1 H); 6.71 (dd, 1 H, 4J=2.1 Hz, 3J=8.9 Hz); 7.09 (d, 4H, 3J=7.9 Hz); 7.14 (d, 4H, 3J=7.9 Hz); 7.30 (d, 1 H, 3J=8.5 Hz); 7.88 (s, 1 H); 11.88 (br s, 1 H); HPLC (METHOD [A]): rt 17.36 min (98.1%)

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

Reference:
Patent; Probiodrug AG; HEISER, Ulrich; RAMSBECK, Daniel; HOFFMANN, Torsten; BOEHME, Livia; (99 pag.)EP2560953; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10364-94-0, The chemical industry reduces the impact on the environment during synthesis 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) and 0.15 mL DMF (dry) was added DBU(0.2 equiv.), and the mixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in 0.5 mL MeCN (dry) was added to the reaction mixture in two portions and it was allowed to stir at 50C for 8 h. MeCN was removed under reduced pressure and the resulting mixture was purified by flashcolumn chromatography (ethyl acetate/petroleum ether = 1:1 to 10:1) to afford benzoylated products.

The chemical industry reduces the impact on the environment during synthesis (1H-Imidazol-1-yl)(phenyl)methanone. I believe this compound will play a more active role in future production and life.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
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 16042-25-4 as follows. 16042-25-4

A mixture of 5-methyl-2- (2-pyridyl)-5 ,6,7 ,8-tetrahydropyrido [4,3 d]pyrimidinetrifluoroacetic acid salt (100 mg, 442 imol, the product of step 2 in Example 34), 1H-imidazole-2-carboxylic acid (74.3 mg, 663 j.imol), HATU (336 mg, 884 imol) and DIPEA (171 mg, 1.33 mmol) in DMF (5 mL) was stirred at rt overnight. The resulting mixture was poured into water and extracted with DCM (30 ml) twice. The combined organic layer was dried over anhydrous Na2504 and concentrated in vacuo and the residue was purified by prep-HPLC to give 1H- imidazol-2-yl-[5-methyl-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone(76 mg) as off-white solid. ?H NMR (400 MHz, Methanol-d4) oe: 8.59-8.8 1 (m, 2H), 8.36-8.48(m, 1H), 7.84-7.97 (m, 1H), 7.36-7.49 (m, 1H), 6.99-7.28 (m, 2H), 6.78-6.94 (m, 0.3H), 5.50-5.88 (m, 1.2H), 4.80-5.01 (m, 0.5H), 3.23-3.69 (m, 1.5H), 3.03 (br d, 1.5H), 1.45-1.77 (m, 3H).MS obsd. (ESI)[(M+H)]: 321.

According to the analysis of related databases, 16042-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (84 pag.)WO2018/83106; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem