Category: 37622-90-5

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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-pyrazolecarboxylate

To a soution of ethyM H pyrazoe4carboxyate (450 mg, 315 mmo) in acetone (63 m) K2C03 (976 mg, T06mmo), 2(choromethy)pyridine hydrochbride (516 mg, 315 mmo) and TBA (119 mg, 032 mmo) was added. The mxture was heated at 6000 overnight. The reaction mixture was cooked and ffltered to remove any soHds. The fitrate was concentrated. Purificaflon by flash chromatography, sflica g&, gradient hexane to ethy acetate afforded the desired product (605 mg, 83% yied) as yeNow oiL 1HNMR (300MHz,CD3), oe ppm: 857 (d, J = 5 Hz, 1H), 803 (s, 1H), 794 (s, 1H), 765 (td, J = 8, 2 Hz,1H), T22 (dd, J = 8,5Hz, 1H), 711 (d, J = 8Hz, 1H), 545 (s, 2H), 430 (q, J 7Hz,2H), t34 (t, J 7 Hz, 3H).

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; LABORATORIOS DEL DR. ESTEVE, S.A.; CUEVAS CORDOBES, Felix; ALMANSA-ROSALES, Carmen; GARCIA LOPEZ, Monica; WO2015/91939; (2015); 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

Preparation 1: Synthesis of 1-(1H-indol-5-yl)pyrazole-4-carboxylic acid ethyl ester; [286] [287] 1H-pyrazole-4-carboxylic acid ethyl ester (1.00g, 7.14mmol) and 1H-indol-5-ylboronic acid (1.15g, 7.14mmol) were dissolved in N,N-dimethylformamide (70mL). Cupper (II) acetate (0.972g, 5.35mmol) and pyridine (1.2mL, 14.8 mmol) were added, and the mixture was stirred for 3 days at room temperature. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography to give the title compound (1.40g, 5.47mmol, 77% Yield). [288] NMR: 1H-NMR(CDCl3) delta 8.39(1H, s), 8.30(1H, br), 8.11(1H, s), 7.92(1H, d), 7.54(1H, dd), 7.47(1H, d), 7.31(1H, t), 6.64-6.62(1H, m), 4.35(2H, q), 1.39(1H, t) [289] Mass(EI) 256(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; LG LIFE SCIENCES LTD.; SONG, Jeong Uk; KIM, Geun Tae; CHOI, Sung Pil; JUNG, Cheol Kyu; PARK, Deok Seong; CHOI, Eun Sil; KIM, Tae Hun; PARK, Hyun Jung; PARK, Wan Su; PARK, Heui Sul; KOO, Ki Chul; ARTEMOV, Vasily; WO2011/43568; (2011); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37622-90-5, 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step A: tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (3.62 g, 13.0 mmol) was combined with ethyl 4-pyrazolecarboxylate (2.0 g, 14 mmol) in 50 mL of DMF. The mixture was cooled to 0 C., and sodium hydride (467 mg, 19.5 mmol) was added. The reaction mixture was then heated at 50 C. for 10 h. Afterwards, it was diluted with diethyl ether (100 ml), washed with water (5×100 mL) and brine (1×10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by MPLC (silica gel, 5-100% EtOAc/hexanes) afforded the desired product. ESI-MS calculated for C16H25O4: 323.39. found 346 (M+Na).

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

Reference:
Patent; Goble, Stephen D.; Mills, Sander G.; Yang, Lihu; Pasternak, Alexander; US2007/238723; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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.

[00615] To the solution of 196-1 (1 g, 7.1 mmol, 1 eq) in EtOH (6 mL) and H20 (10 mL) was added NaOAc (2.2 g, 27.1 mmol, 3.8 eq) and Br2 (5.1 g, 32.1 mmol, 1.7 mL, 4.5 eq). The mixture was stirred at 10 C for 16 hr. The reaction was monitored by TLC. To the reaction mixture was added sodium thiosulfate (2 g), and the solvent was evaporated under reduced pressure. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over Na2S04. The solvent was evaporated under reduced pressure to give 196-2 (1.8 g, crude).

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

Production Example 13-2 tert-Butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate tert-Butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate described in Production Example 13-1 (2.7 g, 9.67 mmol) and commercially available ethyl 4-pyrazole carboxylate (1.49 g, 10.6 mmol) were dissolved in N,N-dimethylformamide (30 mL), 50-72% oily sodium hydride (570 mg) was added at 0 C., and the mixture was heated and stirred at 60 C. for 11 hours. The reaction mixture was cooled to room temperature and water and ethyl acetate were added for partition. The organic layer was washed with water twice and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane, the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1-1:3-0:1), and the target fraction was concentrated under vacuum to obtain the title compound (2.11 g, 68%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.34 (3H, t, J=7.1 Hz), 1.47 (9H, s), 1.82-1.96 (2H, m), 2.10-2.18 (2H, m), 2.82-2.96 (2H, m), 4.19-4.34 (3H, m), 4.29 (2H, q, J=7.1 Hz), 7.91 (1H, s), 7.92 (1H, s).

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; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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.

Compound 103: 1-Methyl-1H-pyrazole-4-carboxylic acid ethyl ester. Under anhydrous condition, to a solution of ethyl 4-pyrazolecarboxylate (3.00 g) in DMF (210 mL, c=0.1 molL-1) cooled by an ice bath, NaH (in mineral oil 60%, 1.10 g, 1.3 equiv.) was added in 3 portions (over 5 minutes). The mixture was stirred for 15 minutes, then methyl iodide (1.6 mL, 1.2 equiv.) was added. The ice bath was removed, and the reaction was stirred at room temperature for 2 Hrs. The mixture was hydrolysed with a saturated aqueous solution of NaHCO3 (1.0 L) and extracted twice with EtOAc (2*1.5 L). The organic layers were combined, washed with brine (0.5 L), dried over MgSO4 and concentrated. Purification by flash-chromatography (AcOEt in cyclohexane, 0 to 90%) afforded compound 103 as a colourless oil in 79% yield (2.60 g). 1H-NMR (400 MHz, DMSO): 1.26 (t, J 7.1 Hz, 3H, O-CH2-CH3); 3.87 (s, 3H, N-CH3); 4.21 (q, J 7.1 Hz, 2H, O-CH2-CH3); 7.82 (s, 1H, Ar); 8.29 (s, 1H, Ar). M/Z (M+H)+ = 155.1.

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

Reference:
Patent; Domain Therapeutics; Mayer, Stanislas; Schann, Stephan; EP2666775; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, 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 37622-90-5 as follows.

To an oven dried, 100 mL round bottom flask was added ethyl 1H-pyrazole-4-carboxylate (3.2 g, 22.8 mmol), Cs2CO3 (8.9 g, 27.4 mmol), 20 mL DMF and ethyl iodide (2 mL, 23.9 mmol). The reaction was stirred for 50 C. for 12 h. 20 mL water was added and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (1×20 mL), brine and dried with Na2SO4 to afford 3.6 grams of ethyl 1-ethyl-1H-pyrazole-4-carboxylate as an oil.

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.)US2015/376136; (2015); 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 37622-90-5

To a solution of 12 4,4,5,5-tetramethyl-2-(2-(3-(trifluoromethyl)benzyl)-1-benzothiophen-7-yl)-1,3,2-dioxaborolane (4) (1.25g, 3.0mmol) and 46 ethyl 1H-pyrazole-4-carboxylate (840mg, 6.0mmol) in 47 pyridine (10mL) was added 48 Cupric acetate, monohydrate (1.19g, 6.0mmol) at room temperature. The mixture was stirred at 50C under a dry atmosphere (CaCl2 tube) overnight. The mixture was quenched with 49 water at room temperature and extracted with EtOAc. The organic layer was separated, washed with 1M HCl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0-25% EtOAc in 50 hexane) to give 51 5 (557mg, 43%) as colorless crystals. 1H NMR (300MHz, CDCl3) delta: 1.39 (3H, t, J=7.1Hz), 4.29 (2H, s), 4.36 (2H, q, J=7.1Hz), 7.08-7.11 (1H, m), 7.38-7.57 (6H, m), 7.68 (1H, dd, J=6.6, 2.2Hz), 8.18 (1H, s), 8.50 (1H, s).

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nakahata, Takashi; Tokumaru, Kazuyuki; Ito, Yoshiteru; Ishii, Naoki; Setoh, Masaki; Shimizu, Yuji; Harasawa, Toshiya; Aoyama, Kazunobu; Hamada, Teruki; Kori, Masakuni; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1598 – 1608;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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. Computed Properties of C6H8N2O2

Ethyl 1-(4-(hydroxymethyl)benzyl)-1H-pyrazole-4-carboxylate Combined ethyl 1H-pyrazole-4-carboxylate (2.31 g; 16.48 mmol; 1.00 eq.), [4-(chloromethyl)phenyl]methanol (2.58 g; 16.48 mmol; 1.00 eq.), DMAP (0.04 g; 0.33 mmol; 0.02 eq.), and potassium carbonate (4.55 g; 32.97 mmol; 2.00 eq.) in acetonitrile (30.00 ml). Heated the reaction to 90 C. for 2 hours. Let the reaction cool to rt. Diluted reaction with water, extracted with ethyl acetate, combined organics, dried with MgSO4, filtered, and concentrated. The residue was purified by silica gel column to give ethyl 1-(4-(hydroxymethyl)benzyl)-1H-pyrazole-4-carboxylate (3.7 g, 86%)1H NMR (400 MHz, Chloroform-d) delta 7.93 (d, J=0.7 Hz, 1H), 7.84 (d, J=0.7 Hz, 1H), 7.40-7.34 (d, J=6.2 Hz, 2H), 7.24 (d, J=6.2 Hz, 2H), 5.29 (s, 2H), 4.70 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 1.36-1.29 (m, 3H).

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, 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. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, 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.

Intermediate 8 -(4-Chloromethyl-benzyl)-1 H-pyrazole-4-carboxylic acid ethyl ester 1 H-Pyrazole-4-carboxylic acid ethyl ester (2 g, 13.9 mmol), (4-chloromethyl-phenyl)- methanol (2.21 g, 13.9 mmol) and triphenylphosphine (4.49 g, 16.8 mmol) are dissolved in tetrahydrofuran (40 ml). The solution is cooled to 0C then diethylazodicarboxylate(6.47 ml, 16.6 mmol) is added. The mixture is stirred at 0C for 2 hours, then 1 hour at room temperature. The solvent is removed under vacuum and the residue is purified by flash chromatography (0 – 50% ethyl acetate in cyclohexane) to give the title compound (Yield 1 .72 g). LC (Method 2): tR = 4.40 min; Mass spectrum (ES+): m/z = 279 [M+H ]+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics