Tag: M.W:200-300

15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate, 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. SDS of cas: 15001-11-3

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 130599-34-7, A common heterocyclic compound, 130599-34-7, name is 3-(4-(Trifluoromethyl)phenyl)-1H-pyrazol-5-amine, molecular formula is C10H8F3N3, 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.

3-Amino-5-(4-trifluoromethyl-phenyl)-pyrazole-l-carboxylic acid tert-butyl ester3-Amino-5-(4-trifluoiOmethyl-phenyl)-pyrazole (2.0 g, 8.8 mmol, 1.0 eq) and KOH 4.5 M (15.7 mL, 70.5 mmol, 8.0 eq) were dissolved in DCM (70 mL), and di- tert-butyl dicarbonate (2.02 g, 9.2 mmol, 1.1 eq) was added; the mixture was stirred at room temperature until complete conversion was observed by LC-MS analysis. The organic phase was washed with saturated brine and evaporated; the crude was crystallized with CH3CN, to give 1.9 g of title product (yield 69%).C15H16F3N3O2 Mass (calculated) [327]; (found) [M+H+] =328. LC Rt = 2.59 min, 100% (5 min method)1H-NMR (dmso-d6): 1.57 (9H, s), 5.83 (IH, s), 6.46 (2H, s), 7.74 (2H, d, J = 8.4 Hz)5 7.95 (2H, d, J = 8.8 Hz)

The synthetic route of 130599-34-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIENA BIOTECH S.P.A.; WYETH PHARMACEUTICALS; WO2008/87529; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1239726-11-4, 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. 1239726-11-4, name is 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis example 174-Bromo-1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carboxylic acid 50 mg (0.21 mmol) of 1 -(2-fluoro-phenyl)-5-methoxy-1 H-pyrazole-3-carboxylic acid were dissolved in 1 .5 ml of acetic acid, sodium acetate (35 mg, 0.42 mmol) and bromine (50 mg, 0.21 mmol) were added and the mixture was stirred for 60 min. The solvent was removed in vacuo and the residue subjected to an aqueous work-up. The obtained crude title compound (60 mg) was used in the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Fluorophenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANOFI; RUF, Sven; PERNERSTORFER, Josef; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; SCHEIPER, Bodo; WIRTH, Klaus; WO2011/92187; (2011); 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. 1239363-40-6, name is 1-Cyclopropyl-4-iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Cyclopropyl-4-iodo-1H-pyrazole

Step 2 In a flask 1-cyclopropyl-4-iodo-1H-pyrazole (405 mg, 1.73 mmol) was dissolved in THF (8.0 mL) and the solution cooled to 0 C. Isopropylmagnesium chloride (2.0 M in THF, 1.04 mL, 2.08 mmol) was added dropwise and the mixture stirred at 0 C. for 45 min, after which 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.53 mL, 2.60 mmol) was added and the mixture allowed to warm to room temperature over 1 h. The mixture was quenched with 50% sat aqueous NH4Cl and extracted with EtOAc. The organic extract was washed with sat. NaCl, dried over MgSO4 and the solution was concentrated. The residue was purified by SiO2 chromatography (20-50% EtOAc/heptane) to afford 405 mg (83%) of 1-cyclopropyl-1H-pyrazole-4-boronic acid pinacol ester as a colorless viscous oil.

According to the analysis of related databases, 1239363-40-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (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. 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 75092-30-7

4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid (301.68 g, 1.2 moles) was slurried in 1.2 L of DCM and DMF (2.3 g, 31 mmol) followed by addition of oxalyl chloride (115 mL, 1.3 moles) over 37 minutes and then stirred at room temperature for 3 h. To the resulting solution was added EtOH (750 mL, 12.9 mol) over 5 min followed by stirring at room temperature for 2 h. The crude product solution was concentrated to dryness in vacuo and then reconstituted in 1.2 L of warm heptane followed by filtration. The filtrate was concentrated by removing 500 mL of heptane, resulting in precipitation of solids. The solids were collected via filtration and dried to afford ethyl 4-iodo-1-methyl-1H-pyrazole-5-carboxylate as a white solid (297.6 g, 89% yield). 1H NMR (CDCl3) delta 7.57 (s, 1H), 4.43 (q, 2H), 4.21 (s, 3H), 1.47 (t, 3H). UPLC (UPLC Method 4): tR=5.10 min. MS (ES+) 280.9 (M+H

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.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); 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. 1125828-30-9, name is 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone, A new synthetic method of this compound is introduced below., Computed Properties of C12H8ClF3N2O

6.2. Preparation of (R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol A 3 L 3-neck jacketed round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged sequentially with dichloro(pentamethylcyclopentadienyl)iridium (III) dimer ([Cp*IrCl2]2, STREM, CAS#: 12354-85-7, 34 mg, 0.043 mmol), (1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine (STREM, CAS#: 144222-34-4, 32 mg, 0.087 mmol), and water (400 mL, 4*) at room temperature. The resulting mixture was stirred for 3 hours at 40 C. to give a homogeneous orange solution. To this active catalyst solution was added potassium formate (145.5 g, 1.73 mol) and a solution of the ketone 1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone (100 g, >99% purity by GC, 0.346 mol) in CH3CN (500 mL, 5*) at 40 C. The reaction mixture was then stirred at 40 C. for 2 h at which time the reaction was determined to be complete by GC. After cooled to 30 C., the aqueous layer (ca. 480 mL) was removed. The organic layer (ca. 600 mL, 6*) was treated with activated carbon (Darco G-60, 20 g, 0.2*) at 45 C. for 2 h and filtered through 1/4 inch bed of Celpure P65 (USP-NF, Pharmaceutical grade, Sigma) and washed with CH3CN (200 mL, 2*). The filtrate was concentrated to 250 mL (2.5*) and transferred to a 2 L 3-neck jacketed round bottom flask equipped with a mechanical stirrer and a temperature controller. More CH3CN (50 mL, 0.5*) was added to increase the solution volume to 300 mL (3*). This solution was warmed to 60 C. and water (500 mL, 5*) was added to this solution at the same temperature. After stirred for 15 minutes at 60 C., the resulting emulsion-like milky mixture was slowly cooled to room temperature. The crystals were then filtered at room temperature, and washed with CH3CN/water (1:2, 150 mL, 1.5*). The wet cake (108 g, KF: 8.83%) was dried under vacuum at 45 C. for 4 h to afford the desired alcohol (white solid, 95 g, 94% yield, >99% chemical purity, >99% ee, KF: 0.014%).

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 73387-52-7, These common heterocyclic compound, 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, 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.

Step 4: Preparation of 4-(3-{[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide A mixture of 5-(4-bromophenyl)-1-methyl-1H-pyrazole (0.50 g, 2.10 mmols,), 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (0.83 g, 2.10 mmols), Tetrakis(triphenylphosphine)palladium(0) (243 mg, 0.10 equivalents), bis[(2-diphenyl-phosphino)]phenyl ether (113 mg, 0.10 equivalents), and 1.0 M potassium tert-butoxide in THF (6.3 mmols, 3 equivalents) in iPrOH (15 mL) that contained 5% water was heated for 4 hours at 90 degrees Celcius in an atmosphere of nitrogen. The reaction mixture was cooled to room temperature and 7 mL of 1N HCl was added. The product was precipitated by the addition of water (30 mL). The precipitate was collected by suction filtration and washed with water (2*20 mL) and cold ethyl ether (4*20 mL). The tan brown solid was dissolved in a small volume of methylene chloride containing 1% methanol and applied to a 140 g cartridge of silica gel. The cartridge was eluted with an acetone:hexane gradient. The appropriate fractions were concentrated and triturated with methanol to produce a white solid (710 mg) as product. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.75-1.84 (m, 3H) 2.40 (d, J=13.54 Hz, 3H) 3.43-3.51 (m, 1H) 3.72 (d, J=11.34 Hz, 3H) 3.84 (s, 3H) 6.40 (d, J=1.46 Hz, 1H) 7.02 (s, 1H) 7.22-7.30 (m, 2H) 7.34 (d, J=8.05 Hz, 1H) 7.38-7.43 (m, 2H) 7.45-7.52 (m, 3H). HRMS calc M+H, 394.1589, found 394.1630.

Statistics shows that 5-(4-Bromophenyl)-1-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 73387-52-7.

Electric Literature of 575452-22-1, 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. 575452-22-1 name is 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, 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.

General procedure: To dry tetrahydrofurane (for 0.019 mol of starting material 40 mL of tetrahydrofurane was used),2.5 M n-BuLi solution in n-hexane (1.1 equiv.) was added dropwise under argon atmosphere at -78C temperature, following by addition of diisopropylamine (1.2 equiv.) at -78 C degree and left tostir at same temperature for 30 min. Then pyrazole 2a, 3a or 5a (1 equiv.) solution intetrahydrofurane (for 0,019 mol of protected pyrazole – 5 mL of THF were used) was added to thereaction mixture at -78 C temperature and left to stir at the same temperature for additional 30 min.Then dimethylformamide (1.3 equiv.) solution in tetrahydrofurane (for 0.025 mol ofdimethylformamide – 5 mL of THF were used) were added dropwise at -78 C degree and left towarm to room temperature overnight. Reaction mixture was cooled down to 5 C temperature andquenched with saturated NH4Cl solution in deionized water (for 0.019 mol of starting material – 12mL of saturated NH4Cl solution were used). Organic layer was separated, inorganic layer wasextracted with dichloromethane (3×10 mL). Organic layers were combined and washed withdeionized water (2×10 mL), dried with anhydrous Na2SO4 and evaporated under reduced pressure.

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

Synthetic Route of 138907-73-0, 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. 138907-73-0, name is Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[1-(4-Fluorophenyl)-1 H-pyrazol-4-yl]acetic acid was prepared from ethyl 1-(4- fluorophenyl)-1 H-pyrazole-4-carboxylate by the procedure outlined in Scheme 5 and using analogous methodology to that described in J. Heterocyclic Chem., 30, 997 (1993).

The synthetic route of Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 153687-35-5, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C12H12N2O2, 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. Safety of 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde

General procedure: The aldehyde (4.62 mmol, 1 equivalent) and 2-methylpropane-2-sulfonamide (0.76 g, 5.55 mmol, 1.2 equivalents) were dissolved in anhydrous THF (10 mL) under an atmosphere of nitrogen with stirring. The concentration of the reaction with respect to the aldehyde was 0.46 M. Tris(2,2,2-trifluoroethyl) borate (1.095 mL, 5.09 mmol) was added dropwise to the stirred reaction mixture at room temperature and the reaction was stirred for approximatively 4 days or until UPLC analysis indicated the reaction was complete. The reaction mixture was diluted with EtOAc (50 mL), washed sequentially with a saturated aqueous solution of NaHCO3 (35 mL) and water (35 mL). The organic layer was then dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the product tert-butyl sulfonyl imines. Some of the products were prone to hydrolysis and unstable to flash chromatography, so were used directly in the subsequent cyclisation step unless specified.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 153687-35-5, its application will become more common.