Category: 35277-02-2

Application of 35277-02-2,Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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 C72 (222 mg, 0.539 mmol) in N,N-dimethylformamide (3 mL) were added cesium carbonate (528 mg, 1.62 mmol) and 4-fluoro-1H-pyrazole (69.6 mg, 0.809 mmol). The reaction mixture was stirred overnight at room temperature, and then at 50 C. for 3 hours, whereupon it was diluted with water and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via chromatography on silica gel (Gradient: 10% to 65% ethyl acetate in heptane) to provide the product as a colorless oil. Yield: 148 mg, 0.455 mmol, 84%. LCMS m/z 326.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.37 (d, J=5.1 Hz, 1H), 7.32 (d, J=4.3 Hz, 1H), 4.88-4.80 (m, 1H), 4.15 (dd, half of ABX pattern, J=10.0, 6.0 Hz, 1H), 4.10 (dd, half of ABX pattern, J=10.2, 4.7 Hz, 1H), 3.68-3.56 (br m, 2H), 3.37-3.26 (m, 2H), 2.28 (dd, half of ABX pattern, J=13.7, 8.6 Hz, 1H), 2.17 (dd, half of ABX pattern, J=13.5, 5.3 Hz, 1H), 1.80-1.59 (m, 3H), 1.59-1.49 (m, 1H), 1.44 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-1H-pyrazole, its application will become more common.

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35277-02-2, name is 4-Fluoro-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 35277-02-2, Formula: C3H3FN2

To a solution of 4-fluoro-pyrazole (0.10 g, 0.001162 mol) in anhydrous THF (10 mL) , which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.16 g, 0.0040665 mol). After addition, the resulting mixture was stirred for three hours. (S)-3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (0.41 g, 0.001162 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water, extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under vacuum.The product was purified by a silica gel column using hexanes and ethyl acetate (2:1 to 1:1) as eluent to afford 0.27 g (64%) of the titled compound as yellowish solid.1H NMR (400 MHz, DMSO-d6) d 10.38 (s, 1H, NH), 8.47 (d, J = 1.6-2.0 Hz, 1H, ArH), 8.24 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H, ArH), 8.10 (d, J = 8.4 Hz, 1H, ArH), 7.74 (d, J = 4.4 Hz, 1H, Pyrazole- H), 7.41 (d, J = 4.4 Hz, 1H, Pyrazole-H), 6.31 (s, 1H, OH), 4.39 (d, J = 14.0 Hz, 1H, CH), 4.21 (d, J = 14.4 Hz, 1H, CH), 1.34 (s, 3H, CH3).Mass (ESI, Positive): 357.11 [M+Na]+.

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-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane, D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (202 pag.)WO2019/222556; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35277-02-2, 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of 5-(4-fluoro-lH-pyrazol-l-yl)pyrazine-2-carbonitrile. (0362) To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-lH-pyrazole (170 mg, 2.0 mmol) and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at 100 C for 4 hours, then cooled to 20 C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (hexane: ethyl acetate = 5: 1) to give 5-(4-fluoro-lH- pyrazol-l-yl)pyrazine-2-carbonitrile (310 mg, 82%). The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Fluoro-1H-pyrazole

To a solution of 4-fluoro-pyrazole (0.10 g, 0.001162 mol) in anhydrous THF (10 mL) , which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.14 g, 0.003486 mol). After addition, the resulting mixture was stirred for three hours. N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide (1056) (0.31 g, 0.001162 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water, extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under vacuum.The product was purified by a silica gel column using hexanes and ethyl acetate (2:1 to 1:1) as eluent to afford 0.37 g (90%) of the titled compound as a yellowish solid.1H NMR (400 MHz, DMSO-d6) d 10.38 (s, 1H, NH), 8.47 (d, J = 2.0 Hz, 1H, ArH), 8.24 (dd, J = 8.8 Hz, J = 2.0 Hz, 1H, ArH), 8.10 (d, J = 8.8 Hz, 1H, ArH), 7.74 (d, J = 4.4 Hz, 1H, Pyrazole- H), 7.41 (d, J = 4.0 Hz, 1H, Pyrazole-H), 6.31 (s, 1H, OH), 4.39 (d, J = 14.0 Hz, 1H, CH), 4.21 (d, J = 14.4 Hz, 1H, CH), 1.34 (s, 3H, CH3).Mass (ESI, Negative): [M-H]-; (ESI, Positive): [M+Na]+.

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.

Adding a certain compound to certain chemical reactions, such as: 35277-02-2, name is 4-Fluoro-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 35277-02-2, name: 4-Fluoro-1H-pyrazole

Step 1: 5-(4-fluoro-1H-pyrazol-1-yl)pyrazine-2-carbonitrile To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100 C. for 4 hours. The reaction mixture was cooled to 20 C., poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane:ethyl acetate=5:1) to give 5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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 35277-02-2 as follows. SDS of cas: 35277-02-2

Step 1 : Benzyl 1-(4-fluoro-1 H-pyrazol-1 -yl)cyclopropanecarboxylate To a solution of 4-fluoropyrazole (125 mg, 1.45 mmol) in tetrahydrofuran (4 mL) at 0C was added sodium hydride (60% suspension in mineral oil, 1 16 mg, 2.90 mmol). The mixture was stirred at 0C for 40 min before benzyl 2,4-dibromobutyrate (0.30 mL, 1.50 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography to afford benzyl 1-(4-fluoro-1 /-/-pyrazol-1-yl)cyclopropanecarboxylate as a clear oil (1 15 mg, 30.4%). 1H NMR (400 MHz, CDCI3) delta 1.64-1.70 (m, 2H), 1.81 -1.86 (m, 2H), 5.14 (s, 2H), 7.22-7.26 (m, 2H), 7.31-7.36 (m, 3H), 7.40 (td, 2H).

According to the analysis of related databases, 35277-02-2, the application of this compound in the production field has become more and more popular.

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 35277-02-2 as follows. Application In Synthesis of 4-Fluoro-1H-pyrazole

In a 100mL single mouth bottle,Add 5-acetyl-2-bromopyridine (1i) (4.00 g, 20 mmol),4-fluoropyrazole (1j) (2.06 g, 24 mmol) and 50 mL of DMF,Reaction at 110 C for 7 hours,The reaction was detected by TLC until the starting point disappeared. After lowering the temperature to room temperature, it was poured into ice water to precipitate a yellow solid, which was washed with a large amount of water, filtered, and dried to obtain 3.31 g of a light yellow solid (1k) with a yield of 81%.

According to the analysis of related databases, 35277-02-2, the application of this compound in the production field has become more and more popular.

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. 35277-02-2, name is 4-Fluoro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Fluoro-1H-pyrazole

7-Bromo-5 -(chloromethyl)-2,3 -dihydro- 1 -benzofuran 3 (120 mg, 0.48 mmol, 1.17 eq.), 4-fluoro-JH-pyrazole (35 mg, 0.41 mmol, leq.), K2C03 (120 mg, 0.87 mmol, 2.1 eq.) in DMF (1 mL) were stirred at rt for 18 hr. The reaction was diluted with water (8 mL) and extracted with EtOAc (10 mL X 2). The combined organics were dried over Na2SO4, and concentrated to give a residue, which was purified by chromatography (SG, hexane/DCM (1.5:1)) to yield 4 as a white solid (106 mg, 88% yield).

According to the analysis of related databases, 35277-02-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC; NUGENT, Richard A.; GURNEY, Mark; MO, Xuesheng; (92 pag.)WO2016/49595; (2016); 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 4-Fluoro-1H-pyrazole

4-Fluoro-1H-pyrazole (4.73 g, 55 mmol) and potassium carbonate (17.27 g, 125 mmol) were combined and stirred in N,N-dimethylformamide (41.7 mL) for 10 minutes in an open sealed tube before addition of 2-bromo-5-acetylpyridine (10 g, 50 mmol). The reaction tube was sealed and stirred 20 hours at 100C. The reaction mixture was then cooled to room temperature and poured into water (700 mL). The mixture was sonicated and stirred for 20 minutes. A beige solid was isolated by filtration, washed with small amounts of water, and dried to yield 1-(6-(4-fluoro-1H- pyrazol-1-yl)pyridin-3-yl)ethan-1-one (9.81 g, 96% yield). MS: M+1 = 206.0.

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.

Related Products of 35277-02-2, 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-Chloro-2-methyl-quinolin-8-ol (30 mg, 0.15 mmol) and 4-Fluoro-lH- pyrazole (Shi, Xifeng; Ishihara, Takashi; Yamanaka, Etairoki; Gupton, John T. Tetrahedron Letters 1995, 36, 1527-1530) (33 mg, 0.39 mmol) in NMP (25 muL) was stirred at 150 C for 90 min. The crude product was purified by reversed phase EtaPLC using a gradient of acetonitrile in water with 0.1 % TFA to give the title compound as the TFA salt. MS (m/z): 244.0 [M+H+]

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