Tag: M.W=0-100

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. 1120-82-7, name is (1H-Pyrazol-1-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: 1120-82-7

General procedure: Step 2: The reaction was performed under argon by using standard Schlenk techniques. To a cold (0?C) solution of 1-(2-hydroxymethyl)-3,5-dimethylpyrazole (1.0?g, 8?mmol) in chloroform was added dropwise thionyl chloride (1.15?mL in 15?mL of CHCl3) and the mixture was refluxed for 4?h. The precipitate (1-(2-chloromethyl)-3,5-dimethylpyrazole, 79% yield) was collected, washed with diethyl ether and dried.

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:
Article; Coelho, Felipe Lange; Dresch, Lucielle Codeim; Stieler, Rafael; Campo, Leandra Franciscato; Schneider, Paulo Henrique; Catalysis Communications; vol. 121; (2019); p. 19 – 26;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, 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 28466-26-4 as follows.

3-(2-(Methoxycarbonyl)phenyl)acrylic acid (1.23 g, 5.97 mmol) was weighed.EDCI (1g, 5.24mmol), DMAP (0.35 g, 2.87 mmol) was dissolved in THF (18 mL) and stirred at room temperature.Compound 1H-pyrazole-4-amine (0.56 g, 5.6 mmol) was then added.The system was stirred at room temperature overnight.Add water to filter the sediment,Concentration in vacuo gave a crude product (yield: 0.72 g, 2.66 mmol) as a white solid.

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing University of Technology; Zhang Na; Qi Xiaoqian; Li Chunqiong; Zhao Lijiao; Zhong Rugang; (8 pag.)CN109879808; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, 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 132712-71-1, Formula: C4H6N2O

General procedure: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.6 6′-amino-3′, 7-dimethyl-1’H-spiro [indeno[1,2-b]quinoxaline-11′,4-pyrano[2,3-c] pyrazole] carbonitrile (8b) Light brown powder (0.35 g, yield 90%). Mp 258-262 C. IR (KBr) 3445, 3250, 3224, 2966, 3110, 2193, 1638, 1597, 1447, 1398. 1H NMR (250 MHz, DMSO-d6): deltaH (ppm) 1.13 (3H, s, CH3), 2.58 (3H, s, CH3-Ar), 7.32-8.14 (9H, m, H-Ar and NH2), 12.6 (1H, s, NH). 13C NMR (62 MHz, DMSO-d6): deltaC (ppm) 8.9 (CH3), 21.1 (CH3-Ar), 56.5 (C-Spiro), 96.3 (C-CN), 118.7 (CN), 121.4, 125.6, 127.8, 128.6, 129.4, 131.5, 132.7, 135.6, 139.7, 140.4, 142.0, 150.8, 152.6, 155.0, 162.4 (C-Ar and C-Pyrazole), 163.3 (C-NH2). Anal. calcd for C23H16N6O: C, 70.40; H, 4.11; N, 21.42. Found: C, 70.44; H, 4.14; N, 21.39.

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-Methyl-1H-pyrazol-5-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Soleimani, Ebrahim; Hariri, Mina; Saei, Parisa; Comptes Rendus Chimie; vol. 16; 9; (2013); p. 773 – 777;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 °C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040percent EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10percent) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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. name: 3-Methylpyrazole

1 – ( [2-(trimethylsilyl)ethoxy]methyl) – lH-pyrazole-3 -carbaldehyde was prepared as follows: 3-Methyl pyrazole (50 g, 0.61 mol) was placed in a 5 L round-bottom flask equipped with mechanical stirrer. 3 L of water was added and heated to 80 C. KMn04 (211.90 g, 1.34 mol) was added portion wise and refluxed for 4.5 h. After stirring at rt overnight, solid was filtered and washed with water. The water was removed in vacuo and 100 mL of water was kept in the flask which was acidified with 1 N HCl to pH 4. It was extracted with EtOAc (2x 1L), washed with brine (2×150 mL), dried over MgS04, filtered and removed in vacuo to yield 1H-pyrazole-3-carboxylic acid (38 g, 56percent) as a white solid. 38 g (0.34 mol) of IH-pyrazole-3-carboxylic acid was refluxed in anhydrous ethanol (1 L) and conc. sulfuric acid (60 mL) for 20 h under nitrogen. Ethanol was removed and crude was basified to pH 8. Precipitated solid was filtered. The filtrate was extracted with THF/CHC13 (2: 3, 3x 1 L), dried over MgS04, filtered and removed in vacuo to yield ethyl 1H-pyrazole-3- carboxylate (39 g, 82percent) as a white solid. To a suspension of ethyl 1H-pyrazole-3-carboxylate (4.42 g, 31.57 mmol) in 1,4-dioxane (140 mL) under N2 atmosphere at 0 C was added NaH (0.91 g, 37.88 mmol) and stirred for 15 min. Neat SEM-Cl (5.79 g, 34.73 mmol) was added drop wise to reaction mixture and stirred overnight at rt. It was quenched with water (30 mL) and excess 1,4-dioxane was removed in vacuo. The residue was extracted with EtOAc (2×250 mL), washed with water (1×50 mL), dried over MgS04, filtered and removed in vacuo to give crude ethyl 1 – {[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.84 g) as a yellow oil. The crude material was used in next step without purification. To a suspension of LiAlH4 in THF (100 mL) at 0 C under N2 atmosphere was added a solution of ethyl 1- f [2-(trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carboxylate (8.88 g, 32.88 mmol) slowly. After addition was completed the cooling bath was removed and reaction mixture was stirred overnight. It was quenched with water (10 mL) carefully at 0 C. THF was removed and residue was diluted with DCM (250 mL) and organic layer was separated, dried over MgS04 and removed in vacuo. The crude material was plugged thru a pad of silica gel with EtOAc/hexanes (from 10percent to 100percent) to yield (1-{[2- (trimethylsilyl)ethoxy]methyl) -lH-pyrazol-3-yl)methanol (5.80 g, 77percent) as an yellow oil. 53.75 g (0.24 mol) of (1- f [2-(trirnethylsilyl)ethoxy]methyl}-1H pyrazol-3-yl)methanol was dissolved in THF and 122.97 g (1.41 mol) of Mn02 was added. The resulting mixture was refluxed for 60 h. Solid material was filtered through a pad of celite and washed with hot THF. The filtrate was removed in vacuo to give crude product. The crude was plugged thru a pad of silica gel and eluted with EtOAc/hexanes (from 20percent to 50percent) to yield 1-{[2- (trimethylsilyl)ethoxy]methyl}-1H pyrazole-3-carbaldehyde (50.88 g, 86.5percent) as a red oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1453-58-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/111001; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 35277-02-2,Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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 C72 (222 mg, 0.539 mmol) in N,N-dimethylformamide (3 mL) were added cesium carbonate (528 mg, 1.62 mmol) and 4-fluoro-1H-pyrazole (69.6 mg, 0.809 mmol). The reaction mixture was stirred overnight at room temperature, and then at 50 C. for 3 hours, whereupon it was diluted with water and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via chromatography on silica gel (Gradient: 10% to 65% ethyl acetate in heptane) to provide the product as a colorless oil. Yield: 148 mg, 0.455 mmol, 84%. LCMS m/z 326.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.37 (d, J=5.1 Hz, 1H), 7.32 (d, J=4.3 Hz, 1H), 4.88-4.80 (m, 1H), 4.15 (dd, half of ABX pattern, J=10.0, 6.0 Hz, 1H), 4.10 (dd, half of ABX pattern, J=10.2, 4.7 Hz, 1H), 3.68-3.56 (br m, 2H), 3.37-3.26 (m, 2H), 2.28 (dd, half of ABX pattern, J=13.7, 8.6 Hz, 1H), 2.17 (dd, half of ABX pattern, J=13.5, 5.3 Hz, 1H), 1.80-1.59 (m, 3H), 1.59-1.49 (m, 1H), 1.44 (s, 9H).

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

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); 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. 694-31-5, name is 1,5-Dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,5-Dimethyl-1H-pyrazole

General procedure: To a solution of pyrazole 1a (50.0 g, 0.45 mol) in pyridine (200 mL,2.6 mol) cooled to 0 C (CF3CO)2O (69.5 mL, 0.50 mol) was added dropwise. The mixture was stirred at r.t. for 12 h. H2O (1000 mL) was added. The formed suspension was washed with CH2Cl2 (3 × 500 mL). The organic layer was dried (Na2SO4), filtered, and evaporated under vacuum. The residue was purified by vacuum distillation (bp 107-110 C/26.7 mbar) to afford pure 2a (78.6 g, 0.38 mmol, 84%) as a yellowish liquid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 694-31-5.

Reference:
Article; Yarmoliuk, Dmytro V.; Arkhipov, Viatcheslav V.; Stambirskyi, Maksym V.; Dmytriv, Yurii V.; Shishkin, Oleg V.; Tolmachev, Andrei A.; Mykhailiuk, Pavel K.; Synthesis; vol. 46; 9; (2014); p. 1254 – 1260;,
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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 288-13-1

General procedure: In a 50 mL round-bottom flask, pyrrole or pyrazole or indole(2.0 mM), 4-iodonitrobenzene (4.4 mM, 1.2 equiv.), Pd(PPh3)4 (2.5mol%) and K2CO3(2.2 equiv.) were added under continuous stirring condition. To this, 5.0 mL of dry DMA was then added under reflux condition at 110 C for 20 h. After completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was allowed to cool at room temperature and diluted with distilled water. After that the solution was extracted with ethyl acetate and the organic layer was dried over anhydrous MgSO4, which was subjected to column chromatography to obtain the corresponding products.

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nandi, Debkumar; Siwal, Samarjeet; Choudhary, Meenakshi; Mallick, Kaushik; Applied Catalysis A: General; vol. 523; (2016); p. 31 – 38;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 36650-74-5, 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. 36650-74-5, name is 1H-Pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 1 -(6-(2-(4-(3-bromopropoxy)-2-methylphenethyl)-5- fluorophenyl)pyridin-2-yl)-5-(trifl uoromethyl)- 1 H-pyrazole-4-carboxylate (400 mg, 0.630 mmol) and 1H-pyrazole-3-carbonitrile (70.4 mg, 0.757 mmol, Fluorochem Products) in acetonitrile (25 mL) was added cesium carbonate (308 mg, 0.946 mmol). The reactionmixture was stirred at 80 00 for 16 hours. The mixture was concentrated under reduced pressure and EtOAc (50 mL) was added. The mixture was filtered through a celite pad and rinsed with EtOAc (2×25 mL). Combined filtrate was concentrated under reduced pressure to afford crude product which was purified by column chromatography eluting with 12-14% EtOAc in hexane to afford ethyl 1-(6-(2-(4-(3-(3-cyano-1H-pyrazol-1-yl)propoxy)-2-methyl phenethyl)-5-fl uorophenyl) pyridin-2-yl)-5-(trifluoromethyl)- 1 Hpyrazole-4-carboxylate (180 mg, 0.274 mmol, 43.5 % yield) as a gummy product. LCMS_rt=4.28min, m/z=647.41 [M+H]

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GOODMAN, Krista B.; KRAUSS, Achim Hans-Peter; LE MONNIER DE GOUVILLE, Anne-Charlotte; DODIC, Nerina; WO2015/33307; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

70A. 2-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine This was prepared from 1B and 5-methyl-1H-pyrazol-3-amine as described for 1C: MS: 249 (M+H)+; HPLC Ret Time: 2.04 min (Phenomenex-Luna S10 4.6*50 mm column, 3 min gradient, 4 mL/min).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2008/9497; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics