Month: September 2021

Related Products of 15802-75-2, 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. 15802-75-2, name is 4-Iodo-3-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol2-iodo-5- (2-iodopyrimidine-3) pyrimidine, 2.0 mmol of 3-methyl-4-iodopyrazole, 0.03 mmol of palladium acetate,0.05 mmol di-t-butyl (2 ‘, 4′, 6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)4.0 mmol of sodium tert-butoxide, and 5 ml of toluene, the reaction tube was purged with nitrogen three times,And then heated to 110 C with an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. Down to room temperatureThe reaction solution was further added, 3.0 mmol of 4-carboxyphenylboronic acid, 0.02 mmol of palladium acetate, 0.04 mmol2′-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1,1’-biphenyl sodium salt, 7.0 mmol sodium carbonate,And 100 mmol of water; then heated to 100 C with an oil bath under magnetic stirring and the reaction was refluxed for 24 hours.Down to room temperature; add 20 ml of water, filtration, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1, room temperature stirring 3h,Filtered, washed with ethanol, dried product 16, yield 72%. The product (C30H22N8O4)Of the mass spectrum (ESI) of 558.20.

The chemical industry reduces the impact on the environment during synthesis 4-Iodo-3-methyl-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Luoyang Normal College; Li Hongmei; Xu Chen; Wang Zhiqiang; Tu Tianyong; Hao Xinqi; (10 pag.)CN106674208; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 34334-96-8,Some common heterocyclic compound, 34334-96-8, name is 3-Methyl-5-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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.

Add acetonitrile (56 mL) to a mixture of 5-methyi-3-nitro-1H-pyrazoie (3.0 g, 22 mniol), potassium carbonate (6.2 g, 2.0 eq), and I -bromo-3-methoxypropane (3.8 g, 1.1 eq). Stir at 65 C overnight. Cool to EtOAc (50 mE) and filter. Concentrate the filtrate in vacuo. Subject the residue to normal phase chromatography, eluting with 35% EtOAc in hexanes, to give the title compound (3.3 g, 70%). MS (ES) ,n/z 200 (M-fH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-5-nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of methyl 2-amino-3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.69 g), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (0.46 g), 2 M aqueous sodium carbonate solution (2.26 mL) and DME (20 mL) was added (1,1-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane adduct (0.09 g) under an argon atmosphere and the mixture was stirred at 80 C. overnight. The reaction mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.65 g). MS: [M+H]+ 336.1

The synthetic route of 1-(4-(Chloromethyl)phenyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Sugimoto, Takahiro; Suzuki, Shinkichi; Sakamoto, Hiroki; Yamada, Masami; Nakamura, Minoru; Kamata, Makoto; Shimokawa, Kenichiro; Ogino, Masaki; Kimura, Eiji; Murakami, Masataka; Kojima, Takuto; Yonemori, Jinichi; (63 pag.)US10548899; (2020); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 78703-53-4 as follows. Application In Synthesis of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 13599-12-7, 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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of 5 (105 g, 573 mmol), K2CO3 (119 g, 860 mmol), and DMF (400 mL) was added benzyl bromide (117 g, 687 mmol). After being stirred at room temperature for 15 h, the mixture was poured into water and extracted with EtOAc. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EtOAc, 100:1 to 4:1) to give 6 (130 g, 83%) as a pale yellow oil.

The synthetic route of Ethyl 3-phenyl-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rikimaru, Kentaro; Wakabayashi, Takeshi; Abe, Hidenori; Imoto, Hiroshi; Maekawa, Tsuyoshi; Ujikawa, Osamu; Murase, Katsuhito; Matsuo, Takanori; Matsumoto, Mitsuharu; Nomura, Chisako; Tsuge, Hiroko; Arimura, Naoto; Kawakami, Kazutoshi; Sakamoto, Junichi; Funami, Miyuki; Mol, Clifford D.; Snell, Gyorgy P.; Bragstad, Kenneth A.; Sang, Bi-Ching; Dougan, Douglas R.; Tanaka, Toshimasa; Katayama, Nozomi; Horiguchi, Yoshiaki; Momose, Yu; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 714 – 733;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175137-46-9, A common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-43-0, 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. 5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 5-amino-1-phenyl-1H-pyrazole-4-carbonitriles (7-12)(0.01 mol) and 20 mL of formic acid was stirred and allowed to reflux for 12 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 13-18 in 68-89% yield. 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (13). Yield: 74%.MP:>300 C. IR (cm-1): 3116; 1727; 1660; 1591. 1H NMR (400 MHz,DMSO-d6, TMS, delta in ppm): 8.06-7.39 (m; 5H; HAr); 8.20 (d; 1H;J=3.8 Hz; H6); 8.34 (s; 1H; H3); 12.46 (s; 1H; NH). 13C NMR(100 MHz, DMSO-d6, TMS, delta in ppm): 107.6 (C3a); 121.7 (C2?, C6?);127.1 (C4?); 129.1 (C3?, C5?); 135.9 (C3); 138.2 (C1?); 148.7 (C6); 151.8(C7a); 157.2 (C4). EI [M+1]+ 213.07.

The synthetic route of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feitosa, Livia M.; da Silva, Edson R.; Hoelz, Lucas V.B.; Souza, Danielle L.; Come, Julio A.A.S.S.; Cardoso-Santos, Camila; Batista, Marcos M.; Soeiro, Maria de Nazare C.; Boechat; Pinheiro, Luiz C.S.; Bioorganic and Medicinal Chemistry; vol. 27; 14; (2019); p. 3061 – 3069;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 706819-66-1, name is 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7BrN2O

General procedure: A 40 mL vial was charged with 5e (640 mg, 1.61 mmol), 12 (546 mg, 1.77 mmol), anhydrous MeCN (15mL) and -325 mesh K2CO3 powder (266 mg, 1.93 mmol). The mixture was stirred at 20 C for 18 h, before being diluted with EtOAc (15 mL) and H2O (15 mL). The phases were separated and the aqueous phase was extracted with additional EtOAc (2 x 10mL). The combined extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica (heptane – EtOAc) to afford 520 mg (52%) of 15d and 410 mg (41%) of 16d.

The synthetic route of 706819-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wright, Stephen W.; Arnold, Eric P.; Yang, Xiaojing; Tetrahedron Letters; vol. 59; 4; (2018); p. 402 – 405;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of aldehyde (2 mmol), 3-aminopyrazole (1 mmol), and p-toluenesulfonic acid catalyst (20 mol percent) in MeCN (5 mL) was magnetically stirred for 24 h in room temperature. Next TsCH2NC (1 mmol) was added and the reaction mixture was stirred for 24 h in room temperature. After completion of the reaction, which was followed by TLC EtOAc/petroleum ether 4:1, the reaction mixture was filtered, and the precipitate washed with methanol. Finally pure solid product was obtained by column chromatography.

The synthetic route of 3-Amino-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rahmati, Abbas; Eskandari-Vashareh, Miranda; Alizadeh-Kouzehrash, Meysam; Tetrahedron; vol. 69; 21; (2013); p. 4199 – 4204;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics