Author: Jessica.F

Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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. 71759-89-2

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 71759-89-2, its application will become more common.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
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

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

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 144689-93-0.

A mixture of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (5.0 g), potassium carbonate (5.75 g), and toluene (50 mL) is stirred at 45-500C for 45 minutes. N-(triphenylmethyl)-5-[4′-(bromomethyl)biphenyl-2- yl]tetrazole (13.2 g) and tetrabutylammonium bromide (1.3 g) are added and the mixture is stirred at 60-70 0C for 10 hours. The insoluble material is removed by filtration and the filtrate is washed with water (2*50 mL) at 60-700C. The filtrate is distilled under vacuum to produce a syrup. Methanol (25 mL) is added to the residue and stirred for 15 minutes at 25-35C. The mass is cooled to 0-5 0C and stirred at that temperature for 45 minutes. The precipitated solid is collected by filtration, washed with methanol (10 mL), and dried at 50-600C for 6 hours (yield 13.3 g).

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, Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below.

Synthesis of Ethyl 1~((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2- carboxylate (lnt~1a) ciInMa2-(Trimethylsilyl)ethoxymethyi chloride (12.8 g, 0.077 mol) was added to a stirred solution of ethyl imidazole-2-carboxylate (9.0 g, 0.064 mol) and potassium carbonate (17.7 g, 0.128 mol) in NtN-dimethylformamide (50 mL) at 0 ¡ãC. The mixture was allowed to stir from 0 ¡ãC to r.t. overnight. Water and ethyl acetate were added and the layers were separated. The separated aqueous layer was extracted with ethyl acetate (X2). The combined organic layers were washed with water (X2). The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo andchromatographic purification (ethyl acetate – hexane) of the residue gave imidazole InMa (12 g, 70percent) as a colorless oil. LCMS m/e (M + H+) – 271.1.

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; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

492-98-8, These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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.

Synthetic example 7: yl)pyridin-2-amine)7A mixture of 1H,17-/-2,2′-biimidazole (840 mg, 6.3 mmol), A/-(4-bromophenyl)-A/- (pyridin-2-yl)pyridin-2-amine (6.59 g, 20.3 mmol) and Cs2C03 (10.14 g, 31.2 mmol) in DMF (70 mL) was degassed (N2 bubbling, 15 min). Cu20 (360 mg, 2.5 mmol) was added and the mixture was heated (140 “C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 35:60:5 then 32:60:8 then 28:60:12) to give Lambda/,Lambda ¡¤(4,4′-(1Eta, 1 “H^’-biimidazoie-l , 1 ‘-diyl)bis(4, 1 -phenylene))bis(A/-(pyridin- 2-yl)pyridin-2-amine) (1.36 g, 35%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/EtOAc/petrol) and then by distillation (sublimation apparatus 260 C, 10~6 mBar): m.p. 218 – 222 C (DSC); ‘H NMR (CDCI3l 400 MHz) delta 6.75 – 6.80 (m, 4H), 6.90 (ddd, J 0.8, 4.9, 7.3 Hz, 4H), 6.93 – 7.00 (m, 8H), 7.09 (d, J 1.0 Hz, 2H), 7.26 (s, 2H), 7.52 (ddd, J 2.0, 7.3, 8.3 Hz, 4H), 8.24 (ddd, J 0.7, 1.9, 4.9 Hz, 4H); 13C NMR (CDCI3, 100 MHz) delta 117.0, 118.6, 121.1 , 125.2, 127.5, 130.0, 133.7, 137.6, 144.3, 148.6, 157.7; HRMS (El) m/z 623.2420 C38H27 10 [M – H]+’ requires 623.2415.

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 492-98-8.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

A solution of 2-(3 ,4-dimethoxyphenyl)-3 -i sopropyl -5 -(piperidin-4-yl)- 1 H-indole, HC1 (25 mg, 0.060 mmol) in DCM (0.5 mL) was neutralized by adding triethylamine drop wise (checked by pH paper). The solution was added to a vial containing i-methyliH-imidazole-5-carbaldehyde (9.95 mg, 0.090 mmol), acetic acid (0.01 ml, 0.175 mmol) at room temperature. The mixture was stirred at room temperature for 16 h. Sodium triacetoxyborohydride (19.15 mg, 0.090 mmol) was added to the reaction mixture and the mixture was stirred for another 6 h at room temperature. The reaction mixture was purified by reverse phase prep LCMS to provide 2-(3,4-dimethoxyphenyl)-3-isopropyl-5-(1 -((1 -methyl- 1H-imidazol-5-yl)methyl)piperidin-4-yl)- 1H-indole (1.27 mg, 4.34% yield,97.2% purity) as a pale solid. LC retention time = 1.734 mm [E]. MS (E) m/z: 473.2 (M+H).

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; HAQUE, Tasir S.; POSS, Michael A.; LOMBARDO, Louis J.; MACOR, John E.; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (296 pag.)WO2018/26620; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 mixture of 10 (1.03 g, 10.7 mmol) and TrCl (3.29 g, 11.8 mmol, 1.1 eq) in MeCN (45 mL) was added Et3N (2.5 mL, 18.0 mmol, 1.7 eq) at rt. After stirring for 2 h, hexane (3 mL) and H2O (40 mL) were added and the mixture was filtered. The resultant cake was washed with water three times and dried in a house vacuumoven at 50 C to afford 18 (3.42 g, 95%) as a white powder.1H NMR (500 MHz, CDCl3) delta 7.10-7.13 (m, 5H), 7.35-7.38 (m, 10H), 7.53 (d, J = 1.1 Hz, 1H), 7.61 (d, J =1.7 Hz, 1H), 9.88 (s, 1H)

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

Reference:
Article; Yamashita, Megumi; Shimizu, Keita; Koizumi, Yasuaki; Wakimoto, Toshiyuki; Hamashima, Yoshitaka; Asakawa, Tomohiro; Inai, Makoto; Kan, Toshiyuki; Synlett; vol. 27; 19; (2016); p. 2734 – 2736;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, The chemical industry reduces the impact on the environment during synthesis 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, A common compound: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

:[0172]A suspension of aminoguanidinium nitrate (150 mg, 1.09 mmol) and K2CO3(150 mg, 1.09 mmol) in N, N-dimethylformamide (DMF) (3 mL) was stirred at room temperature for 1 h. A solution of 1H-benzo [d] imidazole-2-carboxylic acid (162 mg, 1.0mmol) in N, N-dimethylformamide (DMF) (5 mL) was treated with N, N’-carbonyldiimidazole (CDI) (180 mg, 1.1 mmol) at 0. The solution was stirred at room temperature for 1 h. Then it was added to the suspension. The resulting mixture was stirred at room temperature for 3 h , then it was heated to 100 for 3 h. The mixture was cooled to room temperature, filtered and concentrated to give crude 3- (1H-benzo [d] imidazol-2-yl) -1H-1, 2, 4-triazol-5-amine (Intermediate 1) as white solid (290mg, 40purity) which was used in next step directly. Mass spectrum (ESI) m/z calc. for C9H8N6[M+H]+201.08, found 201.20.

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, 1H-Benzimidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; HUANG, Niu; QI, Xiangbing; WANG, Yanli; SUN, Yuze; (56 pag.)WO2017/152842; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem