Category: 1453-58-3

Application of 1453-58-3,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.

To a solution of 3-methyl- 1H-pyrazole (500 mg) in acetonitrile (10 mL) were added di-tert-butyl dicarbonate (1.59 g, 1.7 mL) and DMAP (74.4 mg) at 0°C. The mixture was allowed to warm to rt and was stirred for 2 h. Then, EtOAc was added and the mixture was washed with 0.1 N HC1,saturated NaHCO3 solution and brine, dried with Na2504 and evaporated. The crude product(containing -15percent of tert-butyl 5-methylpyrazole-1-carboxylate) was used in the next reaction step without further purification.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1453-58-3, 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 1453-58-3 as follows.

To a solution of 3-methyl-1H-pyrazole (10.99 g, 134 mmol) in N,N-dimethylformamide (100 ml) at 0° C. was added sodium hydride (3.71 g, 154 mmol, 60percent dispersion). The reaction was stirred at 0° C. for 2 hours. 3-Fluoropyridine (10.0 g, 103 mmol) was added, and the reaction was stirred at 100° C. overnight. The reaction was cooled to room temperature and water was added slowly. The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, concentrated and chromatographed (0-100percent ethyl acetate/hexanes) to afford 3-(3-methyl-1H-pyrazol-1-yl)pyridine (8.4 g, 52.77 mmol, 51.2percent) and 3-(5-methyl-1H-pyrazol-1-yl)pyridine (1.0 g, 6percent). Analytical data of both products is consistent with that reported under Example 6, Step 1.

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow Agrosciences LLC; Niyaz, Noormohamed M.; Garizi, Negar; Zhang, Yu; Trullinger, Tony K.; Hunter, Ricky; Buysse, Ann M.; Kubota, Asako; LePlae, Jr., Paul Renee; Knueppel, Daniel; Lowe, Christian T.; Pernich, Dan; Demeter, David A.; Johnson, Timothy C.; US2013/109566; (2013); 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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., Product Details of 1453-58-3

REFERENCE EXAMPLE 93; Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate; Step b) Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate: A suspension of hexane washed 60percent sodium hydride (3.85 g) in dry dimethylformamide (150 ml) was treated with the dropwise addition of a solution of 3-methylpyrazole (7.75 ml) in dimethylformamide (50 ml) under nitrogen at room temperature. Stirring was continueduntil the gas evolution subsided (10 minutes). A solution of methyl 4-fluoro-2-trifluoromethylbenzoate (17.8 g) fromstep a) in dimethylformamide (50 ml) was added dropwise to the clear solution. After stirring for 30 min. at room temperature the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic extracts (3x) were dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (Merck 60) with a dichloromethane-hexane gradient (50percent – 75percent) to give 13.6 g of the title product as a colorless solid. m.p. 59-61°C MS (EI, m/z): 284 (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; Wyeth; EP1000062; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1453-58-3, These common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, 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-Methyl-1H-pyrazole (1 g, 12.18 mmol), phenylboronic acid (3 g, 24.36 mmol) and pyridine (2 mL, 24.36 mmol) were dissolved (160 mL) and Cu(AcO)2 (3.32 g, 18.27 mmol) and molecular sieves were added and mixture was stirred at r.t. for 48 h. Suspension was filtered through Celite and concentrated and the crude thus obtained was purified by normal phase chromatography using hexane/ethyl acetate from 0% to 7.5% to yield the title compound (83% yield). LRMS: m/z 159 (M+1)+ Retention time: 2.83 min (Method B) 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.38 (s, 3 H) 6.25 (d, J=2.34 Hz, 1 H) 7.18-7.32 (m, 1 H) 7.42 (t, 2 H) 7.65 (dd, J=8.60, 1.17 Hz, 2 H) 7.81 (d, J=2.34 Hz, 1 H).

Statistics shows that 3-Methylpyrazole is playing an increasingly important role. we look forward to future research findings about 1453-58-3.

Reference:
Patent; Almirall, S.A.; Erra Sola, Montserrat; Aguilar Izquierdo, Nuria; Carrascal Riera, Marta; Taboada Martinez, Lorena; Navarro Romero, Eloisa; Vidal Juan, Bernat; EP2390252; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1453-58-3, 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 1453-58-3 as follows.

Preparation of tert-butyl 3-(bromomethyl)-1H-pyrazole-1-carboxylate After 3-methyl-1-pyrazole (2.0 g, 24.3 mmol) was dissolved in acetonitrile (25 mL), tert-butyl dicarbonate (6.5 g, 29.8 mmol) and 4-dimethylaminopyridine (0.31 g, 2.49 mmol) were added thereto at 0° C., and the mixture was slowly warmed to room temperature and then stirred for 2 hours. Ethyl acetate (50 mL) was added to the reaction material, and the result was washed with a 1N aqueous hydrochloric acid solution (50 mL), a saturated aqueous sodium hydrogen carbonate solution (50 mL) and salted water (50 mL), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (ethyl acetate/normal-hexane=1/4) to give tert-butyl 3-methyl-1H-pyrazole-1-carboxylate (4.13 g, 93percent). 1H-NMR (300 MHz, CDCl3) delta 1.64 (s, 9H), 2.34 (s, 3H), 6.17 (s, 1H), 7.96 (s, 1H).

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; US2014/249162; (2014); 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

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. 1453-58-3, name is 3-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Methylpyrazole

250 mL of dimethyl sulfoxide and sodium hydride 24.0 g (60percent, petroleum ether washing) were added to a three-necked flask, and 41.0 g of 3-methylpyrazole was dissolved in 150 mL of dimethyl sulfoxide, and slowly added to the reaction flask. The reaction was carried out until no bubbles were evolved, and 101.5 g of p-methoxybenzyl bromide was added to maintain the temperature of the reaction system at 30 °C. After the reaction was completed, 1 L of ice water was added, and dichloromethane (200 mL × 3) was added, and the organic phase was combined, washed with water, washed with saturated sodium hydrogen carbonate, brine, and dried over anhydrous sodium sulfate.Concentration gave 99.6 g (98.5percent) of 1-(4′-methoxybenzyl)-3-methylpyrazole.

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantong University; Tang Yanfeng; Ding Xinyu; Shan Jiahui; Yu Hongmei; Wang Shuqing; Mao Jiarong; Guo Xiaoqing; (5 pag.)CN103880749; (2019); B;,
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. Recommanded Product: 3-Methylpyrazole

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

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:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1453-58-3, A common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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.

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 ML. The aqueous was chilled to 0 °C, acidified with concentrated HCI, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent).

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 & CO., INC.; WO2004/58702; (2004); A2;,
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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

3-Methyl-1H-pyrazole (0.66 g, 8 mmol) and potassium tertbutoxide (0.88 g, 7.8 mmol) were dissolved in dry dimethyl sulfoxide (DMSO) (5 mL) at room temperature. To the basic solution, 2-bromopyridine (1.17 g, 7.4 mmol) was added slowly under constant stirring, and the solution was heated to reflux under nitrogen for 12 h. Once the reaction completed, it was cooled to room temperature and extracted with water and ether. The organic layer was washed withwater and ether to remove DMSO and excess base. The organic layer was then isolated, dried over anhydrous Na2SO4, and filtered. The solvent was then removed under reduced pressure, and the resultant colorless oil was purified by column chromatography on silica gel (200e300 mesh) eluted with hexane/ethylacetate (9:1 v/v). 1H NMR (500 MHz, CD2Cl2) delta (ppm): 8.43 (1H, d, J 2.53), 8.38 (1H, d, J 4.88), 7.91 (1H, d, J 8.30), 7.79e7.74 (1H, m), 7.59-7.47 (1H, m), 6.25 (1H, d, J 2.53), 2.38 (3H, s).

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; Sunesh, Chozhidakath Damodharan; Subeesh, Madayanad Suresh; Shanmugasundaram, Kanagaraj; Chitumalla, Ramesh Kumar; Jang, Joonkyung; Choe, Youngson; Dyes and Pigments; vol. 128; (2016); p. 190 – 200;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics