Category: 26621-44-3

Electric Literature of 26621-44-3, A common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Under inert gas (eg high purity nitrogen) protection to 10 mlSchlek reaction tube was added 0.02 mmol of water-soluble palladium on water-bound monophosphine salt compound (18), 1.0 mmol of 4-methoxy-2-chloropyridine, 1.5 mmol of 3-nitropyrazole, 3 mmol of potassium carbonate and 5 ml of Water, the reaction tube was replaced with nitrogen three times, and then heated to 100 C with an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. The oil bath was removed and the reaction was concentrated with a rotary evaporator. The residue was chromatographed on silica gel using ethyl acetate as the developing solvent to give pure product 4-methoxy-2-pyridine-3-nitroPyrazole in 85% yield.

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luoyang Normal College; Li Hongmei; Xu Chen; Tu Tianyong; Wang Zhiqiang; Hao Xinqi; (10 pag.)CN106674287; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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. Computed Properties of C3H3N3O2

Production Example 405 4-Bromo-3-nitro-1-trityl-1H-pyrazole 1.42 ML bromine was added at room temperature to a mixture of 3.13 g 3-nitro-1H-pyrazole (compound described in Janssen et al., J. Org. Chem., 36, 3081 (1971)) and 60 ML acetic acid, and the mixture was stirred for 6 hours.. Iced water was added to the reaction solution which was then neutralized with 5 N aqueous sodium hydroxide and an aqueous saturated ammonium chloride solution.. By adding ethyl acetate and water, the aqueous layer was separated.. The aqueous layer was saturated with common salt and extracted with ethyl acetate.. The combined organic layer was washed with an aqueous brine and then dried over anhydrous sodium sulfate.. The drying agent was filtered off, and the filtrate was evaporated. 5.41 g crude product of 4-bromo-3-nitro-1H-pyrazole was obtained as pale brown crystals.. From this compound, 11.05 g of the title compound was obtained as pale brown crystals by the same method as in Production Example 15.1H-NMR (CDCl3) delta: 7.10(m, 6H), 7.27-7.40(m, 9H), 7.46(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26621-44-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 26621-44-3, 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. 26621-44-3 name is 3-Nitro-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.

[313] To a 0 C solution of 3-nitro-1H-pyrazole (250.0 g, 2.17 mol, 1.0 eq) in anhydrous DMF (2.5 L; 10.2 vol eq) under nitrogen was added NaH (95.42 g of 60 %w/w, 2.39 mol, 1.1 eq) in batches over 30 min while maintaining temperature below 8 C. The mixture was stirred for 1 h then 2,4-difluoropyridine (300 mL, 3.29 mol, 1.5 eq) was added, and the reaction was warmed to room temperature and stirred for approximately 16 hours (h). The reaction mixture was diluted with water (12.5 L) and stirred vigorously for 1 h. The off-white solid was collected by vacuum filtration. The solid was re-suspended in water (2 L) and filtered, and this step was repeated once further. The product was dried under vacuum, then suspended in heptane (4L), stirred 3 h at room temperature, and filtered. The solid was washed with two further portions of heptane (2 L each) and dried under vacuum to provide 2-fluoro- 4-(3-nitro-1H-pyrazol-1-yl)pyridine (426.3 g of 92% purity, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 9.01 (d, J = 2.8 Hz, 1H), 8.45 (d, J = 5.7 Hz, 1H), 7.95 (ddd, J = 5.7, 1.9, 1.2 Hz, 1H), 7.81 (t, J = 1.4 Hz, 1H), 7.46 (d, J = 2.8 Hz, 1H) ppm. ESI-MS m/z calc. 208.04, found 209.01 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARIFSON, Paul, S.; COME, Joh, H.; COURT, John, J.; GALE-DAY, Zachary; GU, Wenxin; JACKSON, Katrina, L.; MAGAVI, Sanjay, Shivayogi; NANTHAKUMAR, Suganthini, S.; RONKIN, Steven, Michael; SWETT, Rebecca, Jane; TANG, Qing; (383 pag.)WO2018/107056; (2018); A1;,
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 26621-44-3 as follows. name: 3-Nitro-1H-pyrazole

3-Nitropyrazole (11.3 g, 0.1 mol) at room temperature,Benzyl bromide (17.1 g, 0.1 mol), tetrabutylammonium bromide (1.6 g, 0.005 mol), dissolved in 10 ml of dimethyl sulfoxide (DMSO).Add sodium hydroxide solution [sodium hydroxide solution: 8.8 g (0.22 mol)The solution obtained by dissolving sodium hydroxide in 10 ml of water], the reaction is exothermic,After the dropwise addition is completed, the mixture is stirred at room temperature overnight, and diluted with water to quench.Extract with dichloromethane, dry, concentrate and recrystallize with semi-dry petroleum ether.The product was obtained in 18.3 g with a yield of 90%.

According to the analysis of related databases, 26621-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (16 pag.)CN108863936; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 26621-44-3, 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. 26621-44-3, name is 3-Nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C. solution of 3-nitro-1H-pyrazole (250.0 g, 2.17 mol, 1.0 eq) in anhydrous DMF (2.5 L; 10.2 vol eq) under nitrogen was added NaH (95.42 g of 60% w/w, 2.39 mol, 1.1 eq) in batches over 30 min while maintaining temperature below 8 C. The mixture was stirred for 1 h then 2,4-difluoropyridine (300 mL, 3.29 mol, 1.5 eq) was added, and the reaction was warmed to room temperature and stirred for approximately 16 hours (h). The reaction mixture was diluted with water (12.5 L) and stirred vigorously for 1 h. The off-white solid was collected by vacuum filtration. The solid was re-suspended in water (2 L) and filtered, and this step was repeated once further. The product was dried under vacuum, then suspended in heptane (4 L), stirred 3 h at room temperature, and filtered. The solid was washed with two further portions of heptane (2 L each) and dried under vacuum to provide 2-fluoro-4-(3-nitro-1H-pyrazol-1-yl)pyridine (426.3 g of 92% purity, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 9.01 (d, J=2.8 Hz, 1H), 8.45 (d, J=5.7 Hz, 1H), 7.95 (ddd, J=5.7, 1.9, 1.2 Hz, 1H), 7.81 (t, J=1.4 Hz, 1H), 7.46 (d, J=2.8 Hz, 1H) ppm. ESI-MS m/z calc. 208.04, found 209.01 (M+1).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Bligh, Cavan McKeon; Court, John J.; Liang, Jianglin; O’Dowd, Hardwin; Roeper, Stefanie; Ryan, Michael P.; US2019/177295; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 26621-44-3, name is 3-Nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H3N3O2

To a solution of 3-nitro-1H-pyrazole (3.16 g, 28 mmol) in acetic acid (50 mL) at 0 C was added dropwise fuming HNO3 (2.6 mE, c.a. 58 mmol). Acetic anhydride (6.6 mL, 70 mmcd) was added and the mixture was stirred at it for 3h. The mixture was cooled to 0 C and another portion of fuming HNO3 (0.5 mL, c.a. 11 mmol) was added and the mixture was stirred at it for 2h. The mixture was poured into water, stirred at it overnight, and extracted with EtOAc. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10% EtOAc in petroleum ether to afford 1,3-dinitro-1JJ-pyrazole as a white solid(3.56 g, 81%).

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26621-44-3, name is 3-Nitro-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 26621-44-3, Formula: C3H3N3O2

To a solution of compound 1 (25.0 g, 0.22 mol, 1.0 eq) in THF (250 mL) under Ar protection was added NaH (60%, 9.7 g, 0.24 mol, 1.1 eq) in portions.After stirring at room temperature for 10 min, SEMCl (44.2 g, 0.27 mol, 1.2 eq) was added dropwise.Stir overnight at room temperature.The reaction was quenched with saturated aqueous NH4Cl.The reaction solution was diluted with EtOAc, washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure.Purification by column (PE / EtOAc = 5/1) gave compound 2 (36.3 g, 67%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Longtaishen Pharmaceutical (Nanjing) Co., Ltd.; Yang Lei; (45 pag.)CN110590747; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26621-44-3, name is 3-Nitro-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 26621-44-3, Formula: C3H3N3O2

To a solution of compound 1 (25.0 g, 0.22 mol, 1.0 eq) in THF (250 mL) under Ar protection was added NaH (60%, 9.7 g, 0.24 mol, 1.1 eq) in portions.After stirring at room temperature for 10 min, SEMCl (44.2 g, 0.27 mol, 1.2 eq) was added dropwise.Stir overnight at room temperature.The reaction was quenched with saturated aqueous NH4Cl.The reaction solution was diluted with EtOAc, washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure.Purification by column (PE / EtOAc = 5/1) gave compound 2 (36.3 g, 67%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Longtaishen Pharmaceutical (Nanjing) Co., Ltd.; Yang Lei; (45 pag.)CN110590747; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

26621-44-3, name is 3-Nitro-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. name: 3-Nitro-1H-pyrazole

To a stirred mixture of 3-nitro-lH-pyrazole (3.16 g, 27.9 mmol) in glacial acetic acid (20 mL) at 0 C was added fuming nitric acid (2.6 mL, 58.69 mmol) dropwise, followed by acetic anhydride (6.6 niL, 69.87 mmol). The mixture was stirred and allowed to warm to rt over 3 h, then poured into ice water (50 mL) and stirred for 20 h. The mixture was extracted with EtOAc combined organic layers were dried over MgS04, filtered and concentrated to dryness to afford 1,3-dinitro-lH- pyrazole (4.3 g, 97%). H NMR (300 MHz, DMSO- 6) delta 8.00 (br s, 1H), 6.44 (br s, 1H).

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

26621-44-3, name is 3-Nitro-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. COA of Formula: C3H3N3O2

Referential Example 8 5-(Oxetan-3-yl)-lH-pyrazol-3-amine (91) step 1 : Into a 3 L 4-necked round-bottom flask under nitrogen was placed a solution of 3-nitro-lH- pyrazole (100 g, 884.37 mmol, 1.00 equiv.) in THF (1.5 L), followed by the addition of NaH (53 g, 1.32 mol, 1.50 equiv, 60%> suspension) batchwise at 0C. The resulting solution was stirred at 0 C for 1 h. A solution of [2-(chloromethoxy)ethyl]trimethylsilane (1 17.4 g, 704.17 mmol, 1.20 equiv) in THF (500 mL) was then added dropwise with stirring at 0 C. The resulting solution was stirred at 25 C for 1 h, quenched by the addition of EtOH (200 mL), concentrated under vacuum and diluted with 2 L of EtOAc. The resulting mixture was washed with 2×1 L of brine, dried (Na2S04) and concentrated in vacuo. The residue was triturated with 200 mL of petroleum ether. The solids were collected by filtration and washed with petroleum ether (2 x 500 mL) to afford 125 g (52%) of 3-nitro-l -[[2- (trimethylsilyl)ethoxy]methyl]-lH-pyrazole as a yellow solid.

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics