Day: August 19, 2021

Reference of 39806-90-1, These common heterocyclic compound, 39806-90-1, name is 4-Iodo-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.

To a solution of 4-iodo-1-methyl-1H-pyrazole (3.0 g, 14.4 mmol, 1.0 eq.), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (835 mg, 1.4 mmol, 0.1 eq.) and palladium(II) acetate (415 mg, 0.7 mmol, 0.05 eq.) in dioxane (72.1 ml, 0.2 M) was added N,N’-diisopropylethylamine (5.0 mL, 28.9 mmol, 2.0 eq.) and benzylmercaptan (2.0 ml, 17.3 mmol, 1.2 eq.). The reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with ethyl acetate (300 mL) and water (150 mL). The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography.

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vernier, William F.; Gomez, Laurent; Tetrahedron Letters; vol. 58; 49; (2017); p. 4587 – 4590;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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.

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.

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

Reference of 3469-69-0, A common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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.

General procedure: Step 1: 1-methyl-4-iodopyrazole 1H-4-iodopyrazole (20 g), potassium carbonate (28.45 g) and acetone (120 mL) were added into a round bottomed flask (250 mL) and agitated for 10 min. Then iodomethane (17.56 g) was added and the mixture was agitated at room temperature over night. After that, the mixture was filtrated and concentrated, the residue was recrystallized from n-hexane to prodce 1-methyl-1H-4-iodopyrazole (15 g) as white acicular crystal. 1H-NMR (300Hz, CDCl3) delta: 7.48 (s, 1H), 7.40 (s, 1H), 3.92 (s, 3H).

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute Materia Medica, Chinese Academy Of Sciences; DUAN, Wenhu; GENG, Meiyu; CHEN, Fang; AI, Jing; CHEN, Yi; ZHAN, Zhengsheng; LV, Yongcong; WANG, Ying; DING, Jian; EP2650293; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-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 2075-45-8, HPLC of Formula: C3H3BrN2

To a solution of 4-bromopyrazole (10.0 g, 68.0 mmol) in N,N-dimethylformamide (100 mL) was added dropwise triethylamine (23.7 mL, 170 mmol) under nitrogen atmosphere at room temperature. Trityl chloride (37.9 g, 136 mmol) was added to the reaction solution on an ice bath (0 C.), and stirred for 3 hours at 70 C. Water (400 mL) was added to the reaction solution to precipitate the solids. The precipitated solids were filtered and dried under a reduced pressure. The solids were then azeotropically dried with toluene to obtain the title compound (22.9 g, 87%). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 7.04-7.07 (6H, m), 7.35-7.38 (9H, m), 7.52 (1H, d, J=0.4 Hz), 7.76 (1H, d, J=0.8 Hz).

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-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-40-7, 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. 5334-40-7 name is 4-Nitro-1H-pyrazole-3-carboxylic acid, 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.

4-nitropyrazole-3-carboxylic acid (2.5 g; 15.9 mmol) was added to a stirred solution of aniline (1.6 mL; 17.5 mmol), EDC (3.7 g; 19.1 mmol), and HOBt (2.6 g; 19.1 mmol) in N,N-dimetnylformamide (DMF) (25 ml), then stirred at room temperature overnight.The solvent was removed by evaporation under reduced pressure and the residue triturated with ethyl acetate/saturated NaHCO3 solution.The resultant solid was collected by filtration, washed with water and diethyl ether then dried under vacuum to give 2.85 g of the t itle compound (sodium salt) as a yellow/brown solid.(LC/MS: Rt 2.78, [M+H]+ 232.95).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Nitro-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2005/12256; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 51516-67-7, 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 51516-67-7 as follows.

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.

According to the analysis of related databases, 51516-67-7, the application of this compound in the production field has become more and more popular.

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

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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1,5-dimethyl-1H-pyrazole-4-carboxylic acid (0.063 g, 0.22 mmol), and DIPEA (0.16 mL, 0.51 mmol in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 0.1.02 mmol). The sealed tube was heated to 100 C. for 16 h. The resulting mixture was cooled to room temperature, and partitioned between EtOAc (50 mL) and 50 mL of water. The organic layer was separated and the aqueous layer was extracted with EtOAc (3*25 mL). The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography by 0-5% methanol-dichloromethane to give 1,5-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinol in-6-yl)thiazol-2-yl)-1H-pyrazole-4-carboxamide (0.044 g, 30%). 1H NMR (400 MHz, DMSO-d): delta 12.21 (bs, 1H), 10.18 (s, 1H), 8.30 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.44 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), delta, 3.77 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 2.91 (s, 3H), 2.50 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. For C18H17N5O2S: 367, found 368 (M+1)+.

According to the analysis of related databases, 31728-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, 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. HPLC of Formula: C5H4N2O4

Step 1; To a solution of Compound 14 (60 g, 345 mmol) in methanol (600 mL), under flow of nitrogen, thionyl chloride (75 mL, 1034 mmol) was added at 0C. The solution was then heated at reflux for 4 hours. The reaction mixture was concentrated in vacuo to yield crude product 15 (64.3 g). LC/MS (Method A): 0.93 min, [M+H]+ = 185.

The synthetic route of 1H-Pyrazole-3,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; EP2426135; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 19968-17-3, name is 4-Bromo-3-(trifluoromethyl)-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. Recommanded Product: 4-Bromo-3-(trifluoromethyl)-1H-pyrazole

3-Methyl-4-nitrobenzyl chloride (0.77 g), 4-bromo-3-trifluoromethyl-lH-pyrazole (0.90 g) and po- tassium carbonate (0.57 g) were stirred in DMF (10 ml) at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of so- dium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatogra- phy to obtain 1- (3-methyl-4-nitrobenzyl)-4-bromo-3-trifluoromethyl-lH-pyrazole (0.9 g). ‘H-NMR (CDCl3, ppm): 2.58 (3H, s), 5.35 (2H, s), 7.24-7. 21 (2H, m), 7.49 (1H, s), 7. 98 (1H, d).

The synthetic route of 4-Bromo-3-(trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2005/95351; (2005); 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-1H-pyrazole

A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 mL of N,N-dimethylformamide was stirred at 100C for 8 hours. After cooling to room temperature and adding water, the reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

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; Sumitomo Chemical Company, Limited; EP2145885; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics