Day: June 11, 2021

Some common heterocyclic compound, 151049-87-5, name is 3-Bromo-1-methyl-1H-pyrazole, 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. Formula: C4H5BrN2

Example 0930 0930-1 3-Methoxyazetidine hydrochloride (160 mg), sodium tert-butoxide (250 mg), 1,4-dioxane (10 mL), and ((2-dicyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl))palladium(II) methanesulfonate (BRETTPHOS-PD-G3 (trade name, manufactured by Sigma-Aldrich Co. LLC.)) (40 mg) were added to 3-bromo-1-methyl-1H-pyrazole (160 mg), followed by stirring at 80 C. for 2 hours. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining 3-(3-methoxyazetidin-1-yl)-1-methyl-1H-pyrazole (41 mg) as yellow oily substance. MS m/z (M+H): 168.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 151049-87-5, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, Product Details of 930-36-9

Preparation 17-1) To a stirred mixture of bromine (50.2 ml) in dichloromethane (14) and anhydrous sodium carbonate (206.8 g) was added a solution of N-methylpyrazole (80 g) in dichloromethane (100 ml) at 0~5 C. After stirring for 1 hour at the same temperature, the mixture was stirred for a further one hour at room temperature and then ice cooled. To the reaction mixture, water (1 l) was added. The dichloromethane layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was distilled in vacuo to afford 4-bromo-1-methylpyrazole (150.6 g). bp: 82 C. (20 mmHg) IR (Neat): 3100, 2930 cm-1 NMR (CDCl3, delta): 3.89 (3H, s), 7.38 (1H, s), 7.44 (1H, s) APCI-Mass (m/z): 161, 163 (MH+)

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, 1-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5608056; (1997); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 17635-45-9, 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. 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred suspension of thioacid (1.0 mmol) in THF (5 mL) were added I2 (0.6 mmol, 152 mg), DIPEA (1.2 mmol, 0.156 mL) and HOBt (2.0 mmol, 270 mg) at r.t., followed by the appropriate amine(1.1 mmol). The reaction mixture was stirred for 0.5 to 1 h as analyzed by TLC (until complete disappearance of the thioacid was observed). After the reaction was complete, the solvent was evaporated under vacuum and diluted with EtOAc (20 mL). The organic phase was washed with 10percent HCl (2 × 10 mL), 1 N Na2CO3(3 × 10 mL), H2O (2 × 10 mL) and brine (10 mL) and then dried over anhydrous Na2SO4. The solvent was filtered and evaporated under reduced pressure. The crude reaction mixture was purified under column chromatography using hexane?EtOAc (7:3) as the eluentto afford the desired product.

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-Pyrazol-1-yl-phenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Madhu, Chilakapati; Vishwanatha; Sureshbabu, Vommina V.; Synthesis; vol. 45; 19; (2013); p. 2727 – 2736;,
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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-1H-pyrazol-3-amine

2-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmcl), 1-methyl-I H-pyrazol-3-amine (2) (554mg, 5.7Immol), Xantphos (0.33g, 0.57mmol), and Cs2003 (2.79g, 8.56mmol) were combined in dry 1,4-dioxane (I5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26g,0.28mmol) was then added and the resulting reaction mixture was heated at90°C for 30h. It was then poured onto demineralized water (200mL), and extracted with EtOAc (3 x IOOmL). 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 5-fluoro-N-(1-methyl-IH-pyrazol-3-yl)pyridin-2-amine (3) as a yellow solid (0.65g, 61percent).LCMS (ES): Found 193.0 [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

Application of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

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, 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 277299-70-4,Some common heterocyclic compound, 277299-70-4, name is 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, molecular formula is C12H14N2O, 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.

b 4-{[1-(3,4-Dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]azo}-3-hydroxybenzoic Acid Following the procedure of Example 1, except substituting 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one for 3-methyl-1-(4-methylphenyl)-3-pyrazolin-5-one, the title compound was prepared as an orange solid (1.5 g, 82%). 1H NMR (400 MHz, d6-DMSO) delta 13.5 br s, 1H), 11.0 (s, 1H), 7.70 (m, 2H), 7.61 (dd, J=8.2 and 2.1 Hz, 1H), 7.53 (m, 2), 8.20 (d, J=8.2 Hz, 1H), 2.30 (s, 3H), 2.27 (s, 3H), 2.22 (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 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6642265; (2003); B1;,
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

Electric Literature of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 °C for 10 min. The mixture was then stirred at 60 °C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 °C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10percent NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8percent petroleum ether-EtOAc to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-amino-1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
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 27006-76-4 as follows. Product Details of 27006-76-4

General procedure: To a solution of acetonitrile (20 mL), compound 3 (0.02 mol), benzyltriethylamine chloride (0.001 mol), KOH (0.024 mol), and appropriate phenols were added and refluxed for 5-48 h. The solvent was removed to give a residue under reduced pressure, which was dissolved with CH2Cl2 and washed using 10% KOH solution. Anhydrous MgSO4 was used to dry the dichloromethane layer. Compounds 4a-4l and 5a-5l were obtained after evaporation of the solvents, which were used to prepare compounds 6a-6l and 7a-7l without purification.

According to the analysis of related databases, 27006-76-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Song, Ming-Xia; Wu, Yi; Deng, Xian-Qing; Letters in drug design and discovery; vol. 13; 8; (2016); p. 800 – 808;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (182 mg, 0.60 mmol, 1.0 eq.), cesium carbonate (585 mg, 1.80 mmol, 3.0 eq.), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (173 mg, 0.90 mmol, 1.5 eq.) and Pd(dppf)Cl2.DCM (66 mg, 0.090 mmol, 0.15 eq.) were combined in a vial which was sealed and placed under an inert atmosphere. A 1,4-dioxane/H2O solution (5:1 v/v, 4 mL, degassed) was then added via syringe. The resulting mixture was heated to 90 C. for 1.5 h, after which time the reaction was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure, and crude residue was purified by column chromatography (3-100% EtOAc in hexanes, then 0-5% MeOH in DCM) to give the title compound as a brown solid (22 mg, 11% over 3 steps). ES-MS [M+H]+=334.3.

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

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Engers, Julie L.; Long, Madeline; Bender, Aaron M.; US2020/131180; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics