35277-02-2 | pyrazoles-derivatives

Sep-21 News The important role of 35277-02-2

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

Synthetic Route 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

Extracurricular laboratory: Synthetic route of C3H3FN2

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.

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, category: pyrazoles-derivatives

To a solution of isopropyl (R)-2-amino-2-(4- bromophenyl)-4,4-dimethylpentanoate (420 mg, 1.23 mmol) in dioxane (6 mL) were added 4-fluoro-1H-pyrazole (739 mg, 8.59 mmol), cesium carbonate (3.20 g,9.82 mmol), 2-di-tert-butylphosphino-3 ,4,5,6-tetramethyl-2?,4?,6?-triisopropyl-1,1?-biphenyl (590 mg, 1.23 mmol) and bis(dibenzylideneacetone)palladium(0)(353 mg, 0.61 mmol). The reaction mixture was sparged with argon for 5 mm, andheated at 90 C for 1.5 h. Then to the mixture were added 4-fluoro-1H-pyrazole(317 mg, 3.68 mmol), cesium carbonate (1.60 g, 4.91 mmol), 2-di-tert-butylphosphino-3 ,4,5,6-tetramethyl-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl (354 mg,0.74 mmol) and bis(dibenzylideneacetone)palladium(0) (212 mg, 0.23 mmol). Themixture was sparged and heated at 90 C for 20 h. The reaction mixture was thenpurified by silica gel column chromatography (0-100% gradient EtOAc/hexanes)to give the product.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong R.; CHO, Aesop; BUENROSTRO, Ana Zurisadai Gonzalez; HAN, Xiaochun; JABRI, Salman Y.; MCFADDEN, Ryan; QI, Yingmei; VOIGT, Johannes; YANG, Hong; XU, Jie; XU, Lianhong; (545 pag.)WO2019/75291; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

New learning discoveries about C3H3FN2

Electric Literature of 35277-02-2, The chemical industry reduces the impact on the environment during synthesis 35277-02-2, name is 4-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(4-fluoro- lH-pyrazol- l-yl)propanamide (C14H10F4N4O) (0837) 1029 (0838) [00384] To a solution of 4-fluoro-pyrazole (0.20 g, 0.0023237 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.28 g, 0.0069711 mol). After addition, the resulting mixture was stirred for 3 h. 3- Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)propanamide (1029a, 0.75 g, 0.0023237 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and methanol (19: 1) as eluent to afford 0.75 mg (10%) of the titled compound as white solid. (0839) [00385] Compound 1029 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.81 (s, 1H, NH), 8.25 (d, = 2.4 Hz, 1H, ArH), 8.10 (dd, = 8.8 Hz, = 2.4 Hz, 1H, ArH), 7.95 (d, = 8.8 Hz, 1H, ArH), 7.88 (s, 1H, Pyrazole-H), 7.46 (s, 1H, Pyrazole-H), 4.35 (t, J = 6.0 Hz, 2H, CH2), 2.79 (t, J = 6.0 Hz, 2H, CH2); Mass (ESI, Negative): 325.03 [M-H]

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 35277-02-2

Application of 35277-02-2, The chemical industry reduces the impact on the environment during synthesis 35277-02-2, name is 4-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Sodium hydride (60 wt.%, 276 mg, 6.90 mmol) was added to a mixture of 1- (5-chloropyrazin-2-yl)ethanone (800 mg, 5.11 mmol) and 4-Fluoro-1H-pyrazole (484 mg, 5.62 mmol) in N,N-dimethylformamide (6.0 mL) at ambient temperature for 10 minutes. The reaction mixture was then poured into water (70 mL) and was sonicated and stirred for 20 minutes. A dark red solid was isolated by filtration, washed with small amounts of water, and dried to 1 -(5 -(4-fluoro- 1 H-pyrazol- 1 -yl)pyrazin-2-yl)ethan- 1-one (919 mg, 95% yield). MS: M+1 = 207.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A new synthetic route of 35277-02-2

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.

To a solution of 4-fluoro-1H-pyrazole (0.09 g, 0.001048 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.15 g, 0.003669 mol). After addition, the resulting mixture was stirred for three hours. (R)-3-Bromo-N-(4-cyano-2-iodo-5-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (0.50 g, 0.001048 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 and 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 0.32 g (64%) of the titled compound as a white solid.1H NMR (400 MHz, CDCl3) d 9.60 (s, 1H, NH), 8.76 (s, 1H, ArH), 8.69 (s, 1H, ArH), 7.76 (d, J = 4.8 Hz, 1H, Pyrazole-H), 7.36 (d, J = 4.4 Hz, 1H, Pyrazole-H), 6.85 (s, 1H, OH), 4.39 (d, J = 14.0 Hz, 1H, CH), 4.20 (d, J = 14.0 Hz, 1H, CH), 1.41 (s, 3H, CH3).Mass (ESI, Negative): 481.00 [M-H]-;

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; 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

New learning discoveries about 35277-02-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-1H-pyrazole, and friends who are interested can also refer to it.

Sodium hydride (60 wt.%, 276 mg, 6.90 mmol) was added to a mixture of 1- (5-chloropyrazin-2-yl)ethanone (800 mg, 5.11 mmol) and 4-Fluoro-1H-pyrazole (484 mg, 5.62 mmol) in N,N-dimethylformamide (6.0 mL) at ambient temperature for 10 minutes. The reaction mixture was then poured into water (70 mL) and was sonicated and stirred for 20 minutes. A dark red solid was isolated by filtration, washed with small amounts of water, and dried to 1-(5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-yl)ethan-1-one (919 mg, 95% yield). MS: M+1 = 207.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason D.; GUZI, Timothy; WILSON, Kevin J.; DIPIETRO, Lucian V.; ZHANG, Yulian; WILSON, Douglas; FLEMING, Paul E.; (137 pag.)WO2018/17983; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some scientific research about 35277-02-2

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.

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., Formula: C3H3FN2

2-Chloro-N-[(dimethylamino)methylene]-5-[(diphenylmethylene)amino]pyridine-3-sulfon- amide (1.00 g, 2.34 mmol) was dissolved in DMSO (18 mL). 4-Fluoro-1H-pyrazole (403mg, 4.69 mmol), potassium iodide (389 mg, 2.34 mmol) and potassium phosphate (746 mg, 3.51 mmol) were added and the reaction mixture was stirred overnight at 100CC. Afterwards it was concentrated in vacuo, extracted with dichloromethane/water and the organic phase was washed with brine and dried over sodium sulfate followed by concentration in vacuo.Due to partial deprotection, the material was redissolved in dimethylformamide (2 mL) and stirred overnight with 1 ,1-dimethoxy-N,N-dimethylmethanamine (0.5 mL). The reaction mixture was concentrated in vacuo, extracted with dichloromethane/water and the organic phase was washed with brine and dried over sodium sulfate followed by concentration invacuo to give crude N-[(dimethylamino)methylene]-5-[(diphenylmethylene)amino]-2-(4-fluoro-1 H-pyrazol-1 -yl)pyridine-3-sulfonamide (723 mg).LC-MS (Method A): Rt = 1.25 mm, MS (ESIpos): m/z = 477 [M+H]

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 35277-02-2

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.

Electric Literature 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 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 100C for 4 hours. The reaction mixture was cooled to 20C, 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)pyrazine-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

Share a compound : C3H3FN2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.

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. COA of Formula: C3H3FN2

To a mixture of 60% sodium hydride (56 mg) and THF (15 mL) was added 4-fluoro-1H-pyrazole (103 mg) at 0C. The mixture was stirred at 0C for 1 hr, and to the mixture was added 2,4-difluoro-1l-nitrobenzene (0.110 mL). The mixture was stirred overnight at room temperature, to the mixture was added saturated aqueous ammonium chloride solution at 0C, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, 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 (155 mg). MS: [M+H]+226.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; ITO, Masahiro; SUGIYAMA, Hideyuki; KUBO, Osamu; KIKUCHI, Fumiaki; YASUI, Takeshi; KAKEGAWA, Keiko; IKEDA, Zenichi; MIYAZAKI, Tohru; ARIKAWA, Yasuyoshi; OKAWA, Tomohiro; YONEMORI, Jinichi; TOITA, Akinori; KOJIMA, Takuto; ASANO, Yasutomi; SATO, Ayumu; MAEZAKI, Hironobu; SASAKI, Shinobu; KOKUBO, Hironori; HOMMA, Misaki; SASAKI, Minoru; IMAEDA, Yasuhiro; (500 pag.)WO2019/27054; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Introduction of a new synthetic route about C3H3FN2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.

(5)-N-(2-Chloropyridin-4-yl)-3-(4-fluoro- lH-pyrazol- l-yl)-2-hydroxy-2-methylpropanam (0881) (0882) 1041 (0883) [00407] To a dry, nitrogen-purged 100 mL round-bottom flask equipped with a dropping funnel under argon atmosphere, NaH of 60% dispersion in mineral oil (96 mg, 2.4 mmol) was added in 10 mL of anhydrous THF solvent at ice-water bath. 4-Fluoro-lH-pyrazole (103 mg, 1.2 mmol) was added and the solution stirred 30 min at the ice-water bath. Into the flask, the solution of ( ?)-3-bromo- N-(2-chloropyridin-4-yl)-2-hydroxy-2-methylpropanamide (293 mg, 1.0 mmol) in 5 mL of anhydrous THF was added through dropping funnel under argon atmosphere at the ice- water bath and stirred overnight at RT. After adding 1 mL of H2O, the reaction mixture was condensed under reduced pressure, and then dispersed into 50 mL of EtOAc, washed with 50 mL (x 2) water, evaporated, dried over anhydrous MgS04, and evaporated to dryness. The mixture was purified with flash column chromatography using as an eluent EtOAc/hexane as a 1:2 ratio to produce compounds to produce the titled compound (55%) as a white solid. (0884) [00408] Compound 1041 was characterized as follows: lH NMR (400 MHz, CDCI3) delta 8.90 (bs, 1H, NH), 8.26 (d, = 5.6 Hz, 1H), 7.63 (s, 1H), 7.75 (d, = 4.2 Hz, 1H), 7.33 (d, = 4.2 Hz, 1H), 7.31 (dd, = 5.6, 1.2 Hz, 1H), 5.88 (s, 1H, OH), 4.53 (d, = 13.6 Hz, 1H), 4.14 (d, = 13.6 Hz, 1H), 1.45 (s, 3H); 19F NMR (CDCI3, decoupled) delta -176.47; MS (ESI) m/z 298.98 [M + H] +; 296.96 [M – H] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.