Category: 288-13-1

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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H4N2

At room temperature, pyrazole (0.2 mol) was dissolved in concentrated sulfuric acid (50 mL) and slowly raised to a temperature of 60 CConcentrated nitric acid (9.2 mL) was added and stirring was continued at 60 C for 1.5 hours.After completion of the reaction, the reaction solution was poured into 600 g of ice water, and the resulting white solid was separated by filtration and washed with water.After extraction with ethyl acetate (100 mL x 3), the organic phase was washed successively with 1% sodium bicarbonate solution (100 mL), water (100 mL) and physiological saline (100 mL), dried over anhydrous sodium sulfate and filtered, Finally, the organic phase liquid was rotary evaporated to give a white solid which was combined with the previously obtained white solid to give compound 2a. The resulting compound 2a (12 mmol) was dissolved in DMSO (9 mL)And potassium carbonate (10.9 mmol) was added successively thereto,Methyl iodide (6 mmol),8-hydroxyquinoline (1 mmol),CuI (0.58 mmol). Argon under the conditions of protection, stirMixed and heated to 130 C,After 20 hours of reaction,The reaction solution was poured into an appropriate amount of water,The resulting green solid was separated by filtration.The mother liquor was extracted with ethyl acetate (100 mL x 3). Finally, the organic phase liquid was evaporated to dryness and the resulting crude product was combined with the previously obtained green solid and purified by silica gel column chromatography to obtain Compound 4a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. The compound 8a (1 mmol),EDC (1 mmol), HOBt (1 mmol) was added to DMF(3 mL) for 30 min.The compound 5a, DMAP (1 mmol), triethylamine (500 [mu] L) were added to the activated DMFSolution. At room temperature, stir overnight.After completion of the reaction, 100 mL of saturated sodium chloride solution was added to the reaction solution, and the mixture was washed with ethyl acetateEster extraction (200 mL x 3) extraction. Finally, the organic phase liquid was evaporated under vacuum and evaporated to dryness to obtain a crude product, using a silica gel columnSeparation and purification to give the final compound 9a to give a white solid powder in a yield of 86.4%

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; Nanjing University; Zhu Hailiang; Shi Lu; Wang Zefeng; Wang Chenru; (14 pag.)CN107098861; (2017); A;,
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 288-13-1 as follows. Quality Control of 1H-Pyrazole

Step 1: Preparation of 3-pyrazol-1-yl-pyridine To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere. The reaction mass was refluxed for 24 hrs at 80 C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43%): 1H NMR (400 MHz, CDCl3) delta 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

According to the analysis of related databases, 288-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel I.; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank J.; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; (118 pag.)US2016/60245; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

288-13-1, name is 1H-Pyrazole, 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. HPLC of Formula: C3H4N2

Step 1: Preparation of 3-pyrazol-1-yl-pyridine To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere. The reaction mass was refluxed for 24 hrs at 80 C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43%): 1H NMR (400 MHz, CDCl3) delta 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-13-1, 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 288-13-1 as follows.

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

According to the analysis of related databases, 288-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-13-1, name is 1H-Pyrazole, 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. Quality Control of 1H-Pyrazole

General procedure: General procedure: iodobenzene (1.0mmol), pyrazole (1.5 mmol), LiOH (2.0 mmol), TBAB(0.2 mmol), active Cu (0.1 mmol) and 2 mL H2O were added to a 10 mL flask. The mixture was heated in an oil bath at 120?. When the reaction completed, the resulting mixture was cooled to room temperature and the product was extracted by ethyl acetate (10 mL×3). The combine dextracts were washed by brine (15 mL) , dried over MgSO4 and evaporated under reduced pressure. Further purification by silica gel column chromatography (5:1 petroleum ether/ethylacetate) give 1-phenyl-1H-pyrazole (2a, 0.126 g, 88%) as a Colorless liquid.

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

Reference:
Article; Yang, Qichao; Wang, Yufang; Lin, Dong; Zhang, Mingjie; Tetrahedron Letters; vol. 54; 15; (2013); p. 1994 – 1997;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-13-1, name is 1H-Pyrazole, 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 288-13-1, Recommanded Product: 288-13-1

0535] Preparation of 1-(o-tolyl)-1H-pyrazole [0536] Operating protocol A (82 C., 70 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 383 ?l of 2-iodotoluene (3 mmoles), 136 mg of pyrazole (2 mmoles) and 1.2 ml of acetonitrile. [0537] The degree of transformation and selectivity for 1-(o-tolyl)-1H-pyrazole were 100%. [0538] The residue obtained was purified by silica gel chromatography (eluent: hexane/dichloromethane, 100/0 to 0/100). [0539] 297 mg of a pale yellow oil was obtained, corresponding to a yield of 94% by weight. [0540] The compound obtained had the following formula: [CHEMMOL-00045]

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Cellier, Pascal Philippe; Cristau, Henri-Jean; Spindler, Jean-Francis; Taillefer, Marc; US2003/236413; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 288-13-1, name is 1H-Pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 288-13-1

To a solution of copper(I) oxide (0.906 g, 6.33 mmol), salicylaldoximine (3.47 g, 25.3 mmol), 1H-pyrazole (12.93 g, 190 mmol), and cesium carbonate (66.0 g, 203 mmol) in acetonitrile (50.6 ml) under a nitrogen stream was added 3-bromopyridine (20 g, 127 mmol). The reaction mixture was heated at reflux for 24H. The reaction mixture was allowed to cool to ambient temperature, and then diluted with EtOAc, filtered through celite, and washed with H2O and saturated brine solution. The organics were separated, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-50% acetone in hexanes to afford 3-(1H-pyrazol-1-yl)pyridine as a yellow oil (17 g, 93%): 1H NMR (400 MHz, acetone-d6) delta 9.14 (d, J=2.2 Hz, 1H), 8.54 (d, J=3.8 Hz, 1H), 8.45 (dd, J=2.5, 0.5 Hz, 1H), 8.24 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.79 (d, J=1.5 Hz, 1H), 7.53 (ddd, J=8.3, 4.7, 0.7 Hz, 1H), 6.59 (dd, J=2.5, 1.8 Hz, 1H); EIMS m/z 145.

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 288-13-1.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 288-13-1

General procedure: In a 50 mL round-bottom flask, pyrrole or pyrazole or indole(2.0 mM), 4-iodonitrobenzene (4.4 mM, 1.2 equiv.), Pd(PPh3)4 (2.5mol%) and K2CO3(2.2 equiv.) were added under continuous stirring condition. To this, 5.0 mL of dry DMA was then added under reflux condition at 110 C for 20 h. After completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was allowed to cool at room temperature and diluted with distilled water. After that the solution was extracted with ethyl acetate and the organic layer was dried over anhydrous MgSO4, which was subjected to column chromatography to obtain the corresponding products.

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nandi, Debkumar; Siwal, Samarjeet; Choudhary, Meenakshi; Mallick, Kaushik; Applied Catalysis A: General; vol. 523; (2016); p. 31 – 38;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-13-1, name is 1H-Pyrazole, 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 288-13-1, HPLC of Formula: C3H4N2

Example 56:; N-[6-(2-Hydroxy-2H-pyrazol-3-yl)-2,4-dioxo-7-trifluoromethyl-l,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide; Pyrazol-1-ol; OHHVi N O.A mixture of pyrazole (10 g, 147 mmol) and mCPBA (36.2 g, 147 mmol) in AcOEt (500 mL) was stirred at r.t. for 1O d. The solution was concentrated in vacuo to afford a yellow paste which was extracted with water (6 x 100 mL) and coned HCl (100 mL). The aqueous phase was washed with DCM (2 x 100 mL). The organic layers were combined, concentrated in vacuo and extracted with coned HCl (50 mL). The aqueous phases were combined and 115 g of trisodium phosphate dodecahydrate were added followed by NaOH until pH 10. The aqueous phase was concentrated in vacuo to a volume of 400 mL and was then extracted in continue with OCMfEt2O (2/3) for 40 h. The organic phase was concentrated in vacuo and the residue dissolved in CHCl3. The insoluble material was removed by filtration and washed with EPO chloroform. The aqueous phase was acidified with 200 mL of coned HCl and then extracted continuously with DCMTEt2O (2/3) for 70 h. The organic phases were combined and concentrated in vacuo to afford pyrazol-1-ol (4.7 g, 38%) as a yellow syrup.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 288-13-1, 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. 288-13-1 name is 1H-Pyrazole, 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.

General procedure: Complex 2 (0.05 mmol) was added to a 5 mL of a sealed tube containing the aryl iodide or bromide (0.5 mmol), 1H-pyrazole (0.75 mmol), NaOH (1 mmol), and DMSO (1 mL). The mixture was stirred at 100 C for 12 h. After being cooled to room temperature, the mixture was quenched with 10 mL H2O and extracted with EtOAc(3 × 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography on silicagel with PE/EtOAc (from 10:1 to 5:1) as the eluent to afford the pure products. All N-aryl pyrazoles reported here are known products and were characterised by 1H NMR, and GC-MS.

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

Reference:
Article; Liu, Yan; Liu, Wei; Zhang, Qin; Liu, Ping; Xie, Jian-Wei; Dai, Bin; Journal of Chemical Research; vol. 37; 10; (2013); p. 636 – 637;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics