Day: July 14, 2021

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. 2075-45-8, name is 4-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 2075-45-8

Preparation 45 4-Bromo-1-trityl-1H-pyrazole Trityl chloride (9.02 g) was added to a stirred solution of 4-bromopyrazole (4.24 g) and 4-dimethylaminopyridine (0.711 g) in pyridine (90 ml). The reaction mixture was heated to 85 C. for 20 hrs, cooled to room temperature and partitioned between diethyl ether and water. The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. The crude product was recrystallized from hexane/toluene (5/1, 180 ml) to afford the title compound (4.0 g). The remaining solids and the mother liquors were combined and purified by column chromatography on silica gel eluding with pentane/ether (30/1, v/v) to afford a second batch of title compound (3.0 g). deltaH (300 MHz, CDCl3): 7.60 (1H, s), 7.40 (1H, s), 7.30 (9H, m), 7.20 (6H, m).

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; Pfizer Inc.; US6200978; (2001); B1;,
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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5BrN2

Step A: N-Boc-4-bromo-3-methyl-pyrazole. To 4-bromo-3-methyl-pyrazole (3.50 g, 21.7 mmol) was added CH2Cl2 (30 mL), di-tert-butyl dicarbonate (5.22 g, 23.9 mmol) and aq Na2CO3 (1 M, 43.5 mL). The reaction was stirred for 2.5 h and the aq portion was then separated. The CH2Cl2 portion was then washed with 5% citric acid followed by brine/saturated aq NaHCO3 (1:1). The solution was dried (Na2SO4), filtered and concentrated to afford the product.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clements, Matthew J.; Debenham, John S.; Hale, Jeffrey J.; Madsen-Duggan, Christina B.; Walsh, Thomas F.; Peresypkin, Andrey V.; Helmy, Roy; US2008/269279; (2008); 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 10250-64-3 as follows. Recommanded Product: 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid

General procedure: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

According to the analysis of related databases, 10250-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
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. 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., Formula: C5H8N4O

The mixture of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (70 g, 0.49 mol), EtONa (117 g, 1.72 mol) and the intermediate from Step B ( (272 g, 1.16 mol) in EtOH (1 L) was stirred in a sealed bottle at 120C overnight. The mixture was concentrated and the residue was diluted with H2O (2 L) and then adjusted to pH = 6 with 2 N aqueous HC1 solution. The mixture was extracted with EtOAc (1 L x 3). The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography using petroleum ether/EtOAc = 1 : 1 to give the title product.

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; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1904-31-0, These common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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.

2-Bromopyridine (1) (1 .Og, 6.3mmol), 1-methyl-I H-pyrazol-3-amine (2) (0.79g,8.2mmol), Xantphos (0.37g, 0.63mmol), and Cs2003 (4.Ig, 12.6mmol) were combined in dry 1,4-dioxane (I5mL). The reaction mixture was then degassed with N2(g), and placed under vacuum for 10mm. Pd2(dba)3 (0.29g, 0.3Immol) was added and the resulting reaction mixture was heated at 90°C for 30h. It wasthen poured onto demineralized water (200mL), and extracted with EtOAc (3 x100mL). The organic phases were combined, dried over Na2SO4, filtered and subsequently evaporated under vacuum. The resulting residue was purified by flash chromatography, eluting with EtOAc/Hexane (1:1) to provide N-(1-methyl- I H-pyrazol-3-yl)pyridin-2-amine (3) as a yellow solid (0.75g, 68percent).LCMS (ES): Found 175.2 [MH].

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/72714; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, 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 1904-31-0 as follows.

Example 290a 5-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one 290a A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (100 mL), 1-methyl-1H-pyrazol-3-amine (970 mg, 10.0 mmol), 3,5-dibromo-1-methylpyridin-2-(1H)-one (2.9 g, 11 mmol), and cesium carbonate (6.5 g, 20.0 mmol). After bubbling nitrogen through the suspension for 10 minutes, tris(dibenzylideneacetone)dipalladium(0) (457 mg, 0.50 mmol) and Xantphos (587 mg, 1.0 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 2 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (2 X 50 mL) and the combined organic filtrate was concentrated. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 290a as a yellow solid (900 mg, 32%). MS-ESI: [M+H]+ 283.1

According to the analysis of related databases, 1904-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1310350-99-2, A common heterocyclic compound, 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C5H3ClF2N2O2, 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.

d) 4-Chloro-l-difluoromethyl-lH-pyrazole-3-carboxylic acid methoxy-methyl-amideF A solution of 4-chloro-l-difluoromethyl-lH-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 23 C with N,0- dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HC1 (154 mg, 0.8 mmole) and stirring was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H20, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2: 1) to give the title compound (164 mg) as a colorless oil. MS: m/z = 240.1 [M]+.

The synthetic route of 1310350-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; GABELLIERI, Emanuele; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander V.; ROGERS-EVANS, Mark; ROMBACH, Didier; THOMAS, Andrew; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/126791; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 42027-81-6, 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. 42027-81-6 name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, 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.

Synthesis of compound 22.2. A 50-mL round-bottom flask, was charged with compound 21.1 (100 mg, 0.64 mmol, 1.00 equiv), methanol (5 mL) and palladium on carbon (20 mg). Resulting solution was stirred under H2 gas atmosphere for 1 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to furnish 70 mg (87%) of compound 22.2 as off-white oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; SHELLEY, Mee; MASSE, Craig E.; HARRIMAN, Geraldine C.; WO2015/164374; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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 C4H5BrN2

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).4-bromo-1 ,5-dimethyl-1H-pyrazole10331] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.41 (s, 1H),3.76 (s, 3H), 2.22 (s, 3H)4-bromo-1 ,3-dimethyl-1H-pyrazole10332] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.81 (s, 1H),3.74 (s, 3H), 2.09 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13808-64-5, its application will become more common.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1222174-92-6,Some common heterocyclic compound, 1222174-92-6, name is Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H7BrN2O2, 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 solution of intermediate 2a (506 mg) in dioxane (10 mL) was treated with LiOH solution (2 M, 1 mL) and the mixture was stirred at 70 C for 1 h. HCI (1 M) was added and the mixture was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound (84% yield).LC-MS (Method 2): m/z [M+H]* = 205.0 (MW calc. = 205.01 ); R, = 0.31 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastian; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108336; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics