Category: 3398-16-1

Synthetic Route of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

General procedure: Ethyl 5-(chloromethyl)furan-2-carboxylate (5a, 2.0 g, 10.60 mmol) was added to a solution of 3,5-dimethyl-1H-pyrazole (6a) (1.019 g, 10.60 mmol), KOtBu (1.547 g, 13.79 mmol) and TBAI (0.392 g, 1.060 mmol) in THF (53 ml) at 0 °C. The mixture was allowed to warm up to rt and was stirred at rt for 24 h. To the reaction mixture was added satd NH4Cl aq, and then the mixture was extracted with EtOAc. The organic layers were combined, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (hexane/EtOAc), which yielded the pyrazole 7a (1.25 g, 47.5percent) as a brown oil. Pyrazoles 7b?e were synthesized in a similar way.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuda, Yorinobu; Arakawa, Takeaki; Nawata, Yumi; Shimada, Sayaka; Oishi, Shinya; Fujii, Nobutaka; Nishimura, Shinichi; Hattori, Akira; Kakeya, Hideaki; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1776 – 1787;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

General procedure: The corresponding pyrazole derivative 18, 19 or 22 (4 or 7 equiv) was dissolved in alkaline DMF [containing NaOH (4 or 7 equiv)] and the solution was stirred for 30 min at r.t. The bromomethyl-substituted benzene derivative 21 or 23 (1 equiv) was added and the reaction mixture was stirred for 24?48 h at 70 °C. The solution was cooled to r.t., then poured into ice water (50 mL), and the resulting precipitate was collected by filtration, washed thoroughly with H2O (3 × 15 mL) and dried in a desiccator.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koch, Niklas; Mazik, Monika; Synthesis; vol. 45; 24; (2013); p. 3341 – 3348;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3398-16-1, The chemical industry reduces the impact on the environment during synthesis 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, I believe this compound will play a more active role in future production and life.

4-Bromo-3,5-dimethylpyrazole (3.5714 g, 20 mmol, 98%, 1.0 eq.) was added sequentially to a dry three-neck flask with a magnetic rotor.Phenylboronic acid (2.9552g, 24mmol, 99%, 1.2 equivalents),Palladium acetate (0.1123 g, 0.5 mmol, 0.025 equivalent),Ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equivalents),1,4-Dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 eq.)Aqueous solution (20 mL). nitrogenAir bubbling for 15 minutes,The reaction vial was then placed in a 115 C oil bath.After stirring for 15 hours,The reaction was monitored by thin layer chromatography.Cool to room temperature,Extract with dichloromethane (20 mL x 3).Combine all organic phases,Dry over anhydrous sodium sulfate.Filtered, concentrated,The crude product was purified by flash chromatography on silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3/1 to 1/2) to give 3,5-dimethyl-4-phenylpyrazole, white The solid was 3.0773 g, and the yield was 89%.

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-3,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Feng Qi; Dai Jianxin; Zhao Xiangdong; Chen Shaohai; She Yuanbin; (64 pag.)CN109608506; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, belongs to pyrazoles-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 3398-16-1, Product Details of 3398-16-1

General procedure: 4.4.1. Ethyl 5-amino-2-phenylpyrazolo[1,5-a]quinoline-3-carboxylate (13aa). A mixture of 2-fluorobenzonitrile 6a (121 mg,1.00 mmol), 12a (280 mg, 1.20 mmol) and Cs2CO3 (980 mg,3.00 mmol) in DMSO (5.0 mL) was stirred at 120 C for 16 h. Aftermonitoring the end of the reaction on TLC, the mixture was cooledto room temperature and diluted with water. The resulting mixturewas extracted with ethyl acetate twice. The combined organiclayers were washed with water twice, dried over MgSO4 and thesolvent was removed in vacuo to afford a residue. The residue waspurified by flash column chromatography (hexane:EtOAc1:1) onsilica gel to afford pyrazolo[1,5-a]quinoline 13aa (137 mg, 41percentyield).

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-3,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kato, Jun-Ya; Ijuin, Ryosuke; Aoyama, Hiroshi; Yokomatsu, Tsutomu; Tetrahedron; vol. 70; 17; (2014); p. 2766 – 2775;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3398-16-1, 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. 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a dry three-necked flask with a magnetic rotor was added 4-bromo-3,5-dimethylpyrazole (3.5714 g, 20 mmol, 98%, 1.0 eq.), phenylboronic acid (2.9552 g, 24 mmol, 99%, 1.2 equivalents),Palladium acetate (0.1123 g, 0.5 mmol, 0.025 equivalent), ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equivalent), 1,4-dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 eq.) of aqueous solution (20 mL).Nitrogen was bubbled for 15 minutes and then the reaction flask was placed in a 115 C oil bath.After stirring for 15 hours, the reaction was monitored by thin layer chromatography. It was cooled to room temperature and extracted with dichloromethane (20 mL×3).All organic phases were combined and dried over anhydrous sodium sulfate.Filtration, concentration, and purification of the crude product by flash chromatography on silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3/1 – 1/2) to give 3,5-dimethyl-4-phenyl -1H-imidazole,The white solid was 3.0773 g, and the yield was 89%.

The synthetic route of 4-Bromo-3,5-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Dai Jianxin; She Yuanbin; Chen Shaohai; (127 pag.)CN108659050; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

4.2.6 3,3′,5,5′-Tetrakis[(4-brom-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,2′,4,4′,6,6′-hexamethyldiphenylmethane (35) To a suspension of NaOH (192 mg, 4.81 mmol) in DMF (20 mL), 4-bromo-3,5-dimethyl-1H-pyrazole (841 mg, 4.81 mmol) (37) was added and stirred at room temperature for 20 min. After the addition of compound 20 (500 mg, 0.80 mmol) the reaction mixture was stirred for 72 h at room temperature. Afterwards, the mixture was poured into ice water (200 mL), the formed precipitate filtered off, washed thoroughly with distilled water and dried to constant mass in the desiccator. The desired compound 35 was obtained as a snow-white solid (750 mg, 94percent), mp 216 °C. 1H NMR (500 MHz, CDCl3): delta 5.17 (s, 8H), 4.18 (s, 2H), 2.19 (s, 6H), 2.12 (s, 12H), 2.05 (s, 12H), 2.01 (s, 12H) ppm. 13C NMR (CDCl3, 125 MHz): delta 145.52, 137.86, 137.12, 136.80, 135.81, 130.51, 94.17, 49.69, 33.36, 17.35, 16.53, 12.40, 10.35 ppm. MS (ESI): m/z 1000.8, 827.2, 681.0, 507.0, 333.0. Anal. Calcd for C43H52Br4N8: C, 51.62; H, 5.24; N, 11.20. Found: C, 51.39; H, 5.49; N, 11.38.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koch, Niklas; Rosien, Jan-Ruven; Mazik, Monika; Tetrahedron; vol. 70; 45; (2014); p. 8758 – 8767;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Bromo-3,5-dimethylpyrazole

17.63 g (0.101 mol) of the above intermediate was dissolved in 300 mL of carbon tetrachloride,19.58 g (0.11 mol) of NBS and 0.1 g of benzoyl peroxide were added and heated under reflux for 0.5 h.Stop the reaction, filter after cooling. The filtrate was concentrated and the resulting residue was poured into water and extracted with dichloromethane.The extracted organic phase was washed with saturated brine, dried over anhydrous sodium sulfate,The resulting residue was purified by silica gel column chromatography (silica gel 100-200 mesh, eluent petroleum ether: ethyl acetate = 20: 1)To give 21.2 g of product as a yellow liquid in 84.3percent yield.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Plant Protection Institute; Mei Xiangdong; Dong Mengya; Ning Jun; Zhe Dongmei; Zhang Tao; Zhang Lanxiang; Si Weijie; (13 pag.)CN104610249; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3398-16-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3398-16-1 name is 4-Bromo-3,5-dimethylpyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[00406] To a mixture of 66-1 (1.0 g, 5.7 mmol, 1.00 eq) and K2C03 (1.6 g, 11.4 mmol, 2.00 eq) in DMF (10.0 mL), was added 66-2 (1.9 g, 11.4 mmol, 1.3 mL, 2.00 eq). The resulting mixture was stirred at 60 C for 3H. LCMS showed the reaction was complete. The mixture was diluted with EtOAc (40 mL), washed with water (40 mL *5). The combined organic layers were dried over anhydrous Na2S04, and concentrated under vacuum. 66-3 (1.5 g, crude) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3,5-dimethylpyrazole, and friends who are interested can also refer to it.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

General procedure: Ethyl 5-(chloromethyl)furan-2-carboxylate (5a, 2.0 g, 10.60 mmol) was added to a solution of 3,5-dimethyl-1H-pyrazole (6a) (1.019 g, 10.60 mmol), KOtBu (1.547 g, 13.79 mmol) and TBAI (0.392 g, 1.060 mmol) in THF (53 ml) at 0 °C. The mixture was allowed to warm up to rt and was stirred at rt for 24 h. To the reaction mixture was added satd NH4Cl aq, and then the mixture was extracted with EtOAc. The organic layers were combined, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (hexane/EtOAc), which yielded the pyrazole 7a (1.25 g, 47.5percent) as a brown oil. Pyrazoles 7b?e were synthesized in a similar way.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuda, Yorinobu; Arakawa, Takeaki; Nawata, Yumi; Shimada, Sayaka; Oishi, Shinya; Fujii, Nobutaka; Nishimura, Shinichi; Hattori, Akira; Kakeya, Hideaki; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1776 – 1787;,
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. 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-3,5-dimethylpyrazole

General procedure: The corresponding pyrazole and thallium(I) borohydride in the appropriate ratio (see below) were added to a 500 mL Schlenk tube. The tube was closed with a rubber septum and three vacuum/nitrogen cycles were made. The septum was replaced with a reflux condenser fitted with a bubbler on top. The nitrogen flow was stopped and the stirred solid mixture was slowly warmed using an oil bath (fitted with a temperature regulator) until melting of the pyrazole was observed. At this point, evolution of hydrogen should initiate. The mixture was heated at the corresponding temperature for the required period and then cooled to r.t. During the reaction, some of the unreacted pyrazole sublimed and was deposited over the inside surface of the Schlenk tube. A heating gun was used to melt it and return it to the reaction mixture. The reaction mixture solidified during cooling and was dissolved in CHCl3 before filtration through neutral alumina. The alumina was washed with three portions of CHCl3. The resulting solution was submitted to low pressure in a rotary evaporator to remove the solvent, affording a white solid that was further purified by sublimation to remove the remaining pyrazole. The yields depended strongly on the degree of purity of the starting pyrazole: higher yields were obtained in all cases when the pyrazoles were purified by sublimation instead of by recrystallization prior to being employed as reactants. Thalium Hydrotris(3,5-dimethyl-4-bromopyrazol-1-yl)borate (TlTp*,Br) (1) 1H-4-Bromo-3,5-dimethylpyrazole (14 g, 80 mmol) and thallium(I) borohydride (4.4 g, 20 mmol) were used. The pyrazole melted at 170-175 °C and the reaction was heated at 180 °C for 4 h. Unreacted pyrazole was removed by sublimation (130 °C, 2 mbar) until no more pyrazole was collected. TlTp*,Br was obtained as a white solid in 90percent yield (13.5 g of TlTp*,Br). In contrast, when the initial pyrazole was purified by recrystallization from petroleum ether the final yield of 1 decreased significantly (71percent, 10.6 g of TlTp*,Br).1H NMR (500 MHz, CDCl3): delta = 4.76 (br s, 1 H), 2.37 (s, 9 H), 2.27 (s, 9 H). 11B{1H} NMR (160 MHz, CDCl3): delta = ?7.08 (d, JB-H = 96.6 Hz). 13C{1H} NMR (125 MHz, CDCl3): delta = 146.7 (d, JC-Tl = 33.6 Hz), 143.0, 95.6 (d, JC-Tl = 29.0 Hz), 12.5 (d, JC-Tl = 95 Hz), 12.1. Anal. Calcd for C15H19BBr3N6Tl: C, 24.40; H, 2.59; N, 11.38. Found: C, 24.65; H, 2.58; N, 11.25.

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:
Article; Olmos, Andrea; Pereira, Ana; Belderrain, Tomas R.; Perez, Pedro J.; Synthesis; vol. 50; 17; (2018); p. 3333 – 3336;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics