Category: 5932-27-4

Synthetic Route of 5932-27-4,Some common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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.

Description 11: 1-tert-Butoxvcarbonvlmethvl-1 H-pvrazole-4-carboxylic acid ethyl ester Potassium tert butoxide (0.045g) was added, in portions, to a stirred solution of 3- (ethoxycarbonyl) pyrazole [CAS 37622-90-5] (0.050g) in N, N- dimethylformamide (0. 5mol). The mixture was stirred for 5 min then tert- butylbromoacetate (0.078g) was added, in portions over 2 min. The mixture was stirred for 0.75h then partitioned between ethyl acetate (30moi) and 1. 0M aqueous sodium bicarbonate (20ml). The organic phase was separated, washed with water (2x20m1), dried (Na2SO4) and concentrated in vacuo to give the title compound (0.073g) as a colourless, viscous oil. LC-MS: Rt = 2.78min. Mass Spectrum m/z 255 [MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82862; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5932-27-4, The chemical industry reduces the impact on the environment during synthesis 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

1H-pyrazole-3-carboxylic acid ethyl ester (5.00 g, 35.7 mmol) and K2CO3 (7.40 g, 53.5 mmol) were dissolved in dry DMF (30 mL) in a 100 mL two-necked flask. Ethyl butyrate (5.82 mL, 40.7 mmol) was stirred at room temperature overnight. The reaction was completely detected by TLC. The reaction was quenched by the addition of 150 mL of water, extracted with EA (25mL×4), and the organic phase was combined, concentrated, and purified by silica gel column chromatography (gradient elution polarity: PE/EA=50/1-5/1 ) 4.14g of a colorless transparent liquid, yield 45.6percent,

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, Ethyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, 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 5932-27-4, Application In Synthesis of Ethyl 1H-pyrazole-3-carboxylate

Intermediates 72 and 73Ethyl 1-(2-fluoroethyl)-1H-pyrazole-5-carboxylate and ethyl 1-(2-fluoroethyl)-1H- pyrazole-3-carboxylate To a solution of ethyl 1 H-pyrazole-3-carboxylate (0.77g) (available from ABCR) in acetonitrile (30ml) was added cesium carbonate (1.79g) and the mixture stirred for 5min when 1-fluoro-2-iodoethane (0.96g) was added and the mixture stirred at 200C for 18h.The mixture was evaporated and the residue taken up in water (30ml) and DCM (30ml) separated by hydrophobic frit and concentrated to ~5ml, placed on an SPE cartridge (5Og silica) and eluted with a gradient of ethyl acetate in cyclohexane to give the Ethyl 1-(2- fluoroethyl)-1 H-pyrazole-5-carboxylate (0.42g) as a colourless oil.LC/MS R1 2.09 min m/z 186 [MH+]. Method C and ethyl 1-(2-fluoroethyl)-1 H-pyrazole-3-carboxylate (g) as a colourless oilLC/MS R1 1.73 min m/z 186 [MH+]. Method C

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Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5932-27-4, A common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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.

A 2M aqueous sodium hydroxide solution (1.8 mL, 3.6 mmol) was added to a solution of ethyl 1 H-pyrazole-4-carboxylate (0.2g, 1.55 mmol) in ethanol (4 mL). The reaction mixture was stirred at room temperature overnight and at 80 °C for 2 further hours. The ethanol was evaporated and the mixture was neutralized to give a precipitate which was filtered and dried to give the title compound (0.089 g, 51percent) as a white solid.LRMS (m/z): 113 (M+1)+.

The synthetic route of 5932-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); 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 5932-27-4 as follows. Recommanded Product: Ethyl 1H-pyrazole-3-carboxylate

To a solution of ethyl 3-pyrazolecarboxylate (1.0 g) in N,N-dimethylformamide (7.0 mL) was added N-iodosuccinimide (1.6 g), and the mixture was stirred at room temperature for 1 hour, warmed to 60C, and then stirred for 0.5 hours. The reaction solution was returned to room temperature, saturated aqueous sodium bicarbonate and sodium sulfite were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a compound 0215-1 (1.0 g) as a pale yellow solid.

According to the analysis of related databases, 5932-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 1H-pyrazole-3-carboxylate

To a solution of ethyl 1 H-pyrazole-3-carboxylate (2 g) in MeCN (40 ml) was added cesium carbonate (4.65 g) and the mixture stirred for 30 min when 4-(bromomethyl)tetrahydro-2H- pyran (2.81 g) was added and the mixture stirred at RT for 18 h. The solvent was removed in vacuo and the residue partitioned between dichloromethane (50 ml) and water (20 ml), separated by hydrophobic frit and concentrated. The filtrate was purified by silica (2 x 100 g) cartridge on Flashmaster II using a gradient of DCM and ethyl acetate to give the title compound 1 as a colourless oil, 0.944 g and title compound 2, as a colourless oil, 1 .026g.1 ; LCMS (method B); Rt = 0.90 min, MH+ = 239.2; LCMS (method B); Rt = 0.75 min, MH+ = 239.

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 5932-27-4.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O2

Preparation of Compound 77 Compound 75 was prepared according to J. Heterocycl. Chem., 2003, 487. Compound 75 (10 g, 71.4 mmol), compound 76 (20 g, 89.2 mmol) and K2CO3 (12.328 g, 89.2 mmol) were dissolved in NMP (60 ml), and the mixture was heated to 80° C. for 2 h. The reaction mixture was allowed to cool and diluted with a mixture of ethyl acetate: water=3:1 (500 ml). The water layer was washed with EtOAc (3.x.100 ml), and the organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified on silica gel (PE:EA=100:1 to 20:1) to give compound 77 as yellow oil (2.2 g, 10.9percent). 1H NMR (400 MHz, CDCl3): 0.860 (q, 6H, J=4 Hz), 0.978 (m, 1H), 1.213 (m, 1H), 1.372 (t, 3H, J=7.2 Hz), 1.555 (m, 2H), 2.329 (m, 2H), 3.709 (s, 3H), 4.334 (q, 2H, J=7.2 Hz), 5.907 (q, 1H, J=5.2 Hz), 6.896 (d, 1H, J=2 Hz), 7.587 (d, 1H, J=2 Hz). MS-ESI: m/z=283.1 [M+1]+.

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; INTERMUNE, INC.; US2009/257979; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5932-27-4, The chemical industry reduces the impact on the environment during synthesis 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

To a suspension of Cs2CO3 (2100 g, 6.44 mol) in DMF (12 L) was added ethyl 1H-pyrazole-3-carboxylate (750 g, 5.36 mol), followed by 2-chloroacetonitrile (450 g,5.96 mol) and the mixture was stirred at about 25° C. for about 16 hrs. The reaction was poured into water (12 L) and extracted with EtOAc (5×5 L). The combined EtOAc extracts were washed with brine (2×5 L), dried (Na2SO4) and concentrated to afford a residue which was purified by chromatography to afford ethyl 1-(cyanomethyl)-1H-pyra- zole-3-carboxylate (398 g, 39percent) as a yellow oil and ethyl 1 -(cyanomethyl)- 1 H-pyrazole-5-carboxylate (680 g). The ethyl 1 -(cyanomethyl)- 1 H-pyrazole-5-carboxylate was dissolved in MTI3E (15 L) and washed with brine (3×5 L), dried (Na2SO4) and concentrated to afford the compound as a yellow oil (489 g, 5 1percent). ?H NMR (400 MHz, CDCl3) delta: 7.49 (s, 1H), 6.82 (s, 1H), 5.45 (s, 2H), 4.29 (q, 2H), 1.29 (t, 3H)10138] LCMS mlz=180.1 [M+H]+

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, Ethyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5932-27-4, These common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, 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.

1 – ( [2-(trimethylsilyl)ethoxy]methyl) – lH-pyrazole-3 -carbaldehyde was prepared as follows: 3-Methyl pyrazole (50 g, 0.61 mol) was placed in a 5 L round-bottom flask equipped with mechanical stirrer. 3 L of water was added and heated to 80 C. KMn04 (211.90 g, 1.34 mol) was added portion wise and refluxed for 4.5 h. After stirring at rt overnight, solid was filtered and washed with water. The water was removed in vacuo and 100 mL of water was kept in the flask which was acidified with 1 N HCl to pH 4. It was extracted with EtOAc (2x 1L), washed with brine (2×150 mL), dried over MgS04, filtered and removed in vacuo to yield 1H-pyrazole-3-carboxylic acid (38 g, 56percent) as a white solid. 38 g (0.34 mol) of IH-pyrazole-3-carboxylic acid was refluxed in anhydrous ethanol (1 L) and conc. sulfuric acid (60 mL) for 20 h under nitrogen. Ethanol was removed and crude was basified to pH 8. Precipitated solid was filtered. The filtrate was extracted with THF/CHC13 (2: 3, 3x 1 L), dried over MgS04, filtered and removed in vacuo to yield ethyl 1H-pyrazole-3- carboxylate (39 g, 82percent) as a white solid. To a suspension of ethyl 1H-pyrazole-3-carboxylate (4.42 g, 31.57 mmol) in 1,4-dioxane (140 mL) under N2 atmosphere at 0 C was added NaH (0.91 g, 37.88 mmol) and stirred for 15 min. Neat SEM-Cl (5.79 g, 34.73 mmol) was added drop wise to reaction mixture and stirred overnight at rt. It was quenched with water (30 mL) and excess 1,4-dioxane was removed in vacuo. The residue was extracted with EtOAc (2×250 mL), washed with water (1×50 mL), dried over MgS04, filtered and removed in vacuo to give crude ethyl 1 – {[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.84 g) as a yellow oil. The crude material was used in next step without purification. To a suspension of LiAlH4 in THF (100 mL) at 0 C under N2 atmosphere was added a solution of ethyl 1- f [2-(trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.88 g, 32.88 mmol) slowly. After addition was completed the cooling bath was removed and reaction mixture was stirred overnight. It was quenched with water (10 mL) carefully at 0 C. THF was removed and residue was diluted with DCM (250 mL) and organic layer was separated, dried over MgS04 and removed in vacuo. The crude material was plugged thru a pad of silica gel with EtOAc/hexanes (from 10percent to 100percent) to yield (1-{[2- (trimethylsilyl)ethoxy]methyl) -lH-pyrazol-3-yl)methanol (5.80 g, 77percent) as an yellow oil. 53.75 g (0.24 mol) of (1- f [2-(trirnethylsilyl)ethoxy]methyl}-1H pyrazol-3-yl)methanol was dissolved in THF and 122.97 g (1.41 mol) of Mn02 was added. The resulting mixture was refluxed for 60 h. Solid material was filtered through a pad of celite and washed with hot THF. The filtrate was removed in vacuo to give crude product. The crude was plugged thru a pad of silica gel and eluted with EtOAc/hexanes (from 20percent to 50percent) to yield 1-{[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carbaldehyde (50.88 g, 86.5percent) as a red oil.

Statistics shows that Ethyl 1H-pyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 5932-27-4.

Reference:
Patent; ASTRAZENECA AB; WO2005/111001; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5932-27-4, 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 16: Ethyl 1 -U2-(putyloxy)phenyl1methyl’HH-pyrazole-3- carboxylate; To ethyl 1 H-pyrazole-3-carboxylate (1.74 g, 12.4 mmol, ChemCollect GmbH) and potassium carbonate (3.43 g, 24.8 mmol) was added 1-(bromomethyl)-2- (butyloxy)benzene (3.0 g, 12.3 mmol) as a solution in DMF, washing in with further DMF to give a total volume of 35 ml. The mixture was stirred under nitrogen at ambient temperature. After 24 h the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and water (approximately 100 ml each). The layers were separated and the aqueous was extracted with further EtOAc (2 x 50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give a pale yellow oil, which partially solidified on standing. The material was loaded in dichloromethane and purified on silica (Si) 100 g using 0- 100percent ethyl acetate-cyclohexane. The appropriate fractions were combined and concentrated in vacuo to give the title compound (2.07 g); LCMS: (System 4) MH+ = 303, tRET = 3.27 min.

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

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics