Category: 112758-40-4

Related Products of 112758-40-4, 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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-(2-(3-isobutyryl-1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; intermediate 6 To a solution of 3-methyl-1H-pyrazole-4-carbaldehyde (273 mg, 2.48 mmol) in anhydrous DMF (5 mL) was added 60% NaH (130 mg, 3.25 mmol) at 0 C. After being stirred for 30 min at room temperature, it was cooled to 0 C. To this, was added intermediate 5 (542 mg, 1.65 mmol) and then stirred for 6 hours at 60 C. Quenching the reaction by addition of ice and 20 mL of water resulted precipitation of brown solids. The resulted solids were collected by filtration, rinsed with water and the dried in vacuo to provide the desired intermediate 6 as a brown solid (424 mg, 80%); MS (ESI) m/z 403 [M+H]+.

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-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); 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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O

In a 250-mL round-bottom flask, to a solution of 3-methyl- lH-pyrazole-4-carbaldehyde (2.2 g, 18.98 mmol, 1.00 equiv) in DMF (40 mL) was added sodium hydride (60% in oil, l .2g, 30.0 mmol, 1.58 equiv) at 0 C. The mixture was stirred for 1 h at room temperature, and then was added by 4-bromooxane (4 g, 23.03 mmol, 1.21 equiv). The reaction mixture was then stirred overnight at 120 C. When the reaction was done, it was quenched by the addition of water (20 mL) and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by reverse phase flash chromatography eluting with MeOH in water (10% to 40% gradient in 60 min) to give a mixture of 3 -methyl- l-(tetrahy dro-2H-pyran-4-yl)-lH- pyrazole-4-carbaldehyde and 5-methyl-l -(tetrahydro-2H-pyran-4-yl)-l H-pyrazole-4- carbaldehyde as yellow oil (1.2 g, 1 :1 , 33%). MS: m/z = 195.2 [M+H]+

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 112758-40-4.

Reference:
Patent; MERCK PATENT GMBH; CALDWELL, Richard; LIU-BUJALSKI, Lesley; POTNICK, Justin; NEAGU, Constantin; KULKARNI, Shashank; JONES, Reinaldo; QIU, Hui; (238 pag.)WO2020/43638; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4,Some common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Preparation of 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; Intermediate 1 To a solution of ethyl 3-methyl-1H-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N-dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature. The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (*2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 1 as a white solid (5.47 g, 42%); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCl3) delta 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, J=5.4 Hz), 7.87 (1H, d, J=5.4 Hz), 2.59 (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 3-Methyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4, These common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

PREPARATION 461-(3-Chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde; To a solution of 3-methyl-pyrazole-4-carbaldehyde (0.5 g, 4.5 mmol) in dry dimethylformamide (15 mL) is added potassium carbonate (2.5 g, 18 mmol,) at room temperature. The reaction mixture is stirred at 40 C. for 30 min and then 1-fluoro-2-chloropyridine (0.77 g, 6 mmol,) is added. The reaction mixture is heated at 70 C. for 16 h. After completion, the reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture is purified by chromatography on silica gel eluting with hexane/ethyl acetate (75:25, 65:35) to yield 0.525 g (52%) of the title compound. MS (m/z): 222 (M+1).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; US2011/118251; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 112758-40-4, 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. 112758-40-4 name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

To a solution of 3 -methyl- lH-pyrazole-4-carbaldehyde (1 g, 9.08 mmol) in acetonitrile (10 mL) is added potassium carbonate (1.76 g, 12.71 mmol) and 2,3- difluornitrobenzene (1.73 g, 10.90 mmol) and the mixture is stirred at room temperature overnight. Water is added and the organic phase is extracted with ethyl acetate. Organic layer is dried over sodium sulfate and the solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate/hexane (20-80%) to give a 62% yield of a mixture of regioisomers containing the title compound as major product that is used with no further purification. NMR is consistent with desired structure, although mixture of regiosomers is detected: NMR (MeOD): 9.98 (s, 1H), 8.65 (d, 1H, J= 1.6 Hz), 7.99-7.26 (m, 3H), 2.49 (s, 3H). A solution of 2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine] (2.1 g, 7.5 mmol) and l-(2-fluoro-6-nitro-phenyl)-3-methyl-pyrazole-4-carbaldehyde (3 g) (as major compound in a mixture of regioisomers in the pyrazole) in dichloromethane (47 mL) is stirred at room temperature for 30 minutes. Then, sodium triacetoxy borohydride (3.94g) is added and the mixture is stirred overnight at that temperature. The reaction mixture is quenched carefully with sodium bicarbonate (saturated solution) and extracted with dichloromethane. Organic layer is washed with brine, decanted and dried over sodium sulfate. Solvent is evaporated and the residue is purified by normal phase Isco chromatography using as eluant dichloromethane and isopropanol to give 2.28 g of 2-chloro-4,4-difluoro- -[[l-(2-fluoro-6-nitro-phenyl)-3-methyl-pyrazol-4- yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine] (the compound is contaminated with the other pyrazole regioisomer in a ratio 80:20). MS (m/z): 513 (M+l).

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

Reference of 112758-40-4, 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. 112758-40-4 name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

A screw-cap test tube containing molecular sieves (4A) and a solution of 3- methyl-lH-pyrazole-4-carbaldehyde (100 mg, 0.91 mmol), 2,6-dimethylphenylboronic acid (150 mg, 1 mmol), copper(II) acetate (247 mg, 1.36 mmol) and pyridine (147 mu, 1.8 mmol) in dry dichloromethane (4.5 mL) is shaked at room temperature for 48 hr. The mixture is filtered over celite, washed with methanol and the solvent evaporated in vacuo. Resulting product is purified by silica gel using normal phase Isco chromatography eluting with hexane: acetone (gradient from 5 to 30% in acetone) to give 67 mg of the title compound. MS (m/z): 215 (M+l)

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

Electric Literature of 112758-40-4, 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. 112758-40-4 name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

A mixture of 3 -methyl- lH-pyrazole-4-carbaldehyde (5 g, 45.41 mmol), potassium carbonate (9.41 g, 68.11 mmol), 2,3-difluorobenzonitrile (6.06 mL, 54.5 mmol) and dimethylformamide (50 mL) is stirred at 100C for 5 hr. and then at room temperature overnight. Water is added and a precipitated is formed. The precipitate is filtered. The aqueous solution filtered is extracted in ethyl acetate. Organic layer is washed with brine, dried over magnesium sulfate and solvent is evaporated. Both the solid precipitated and the solid recovered from organic layer after evaporation are combined and 10.4 g of the title compound is obtained and used with no further purification (the title compound is contaminated with the other pyrazole regioisomer in a ratio 90: 10). MS (m/z): 230 (M+l). To a suspension of 2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′- piperidine] hydrochloride (1.3 g, 4.11 mmol) in 1,2-dichloroethane (20.5 mL) is added triethylamine (0.75 mL, 5.3 mmol) and 3-fluoro-2-(4-formyl-3-methyl-pyrazol-l-yl)- benzonitrile (as major compound in a mixture of regioisomers) (1.13 g, 4.93 mmol). The mixture is stirred at room temperature for 30 min. Then, sodium triacetoxyborohydride (1.82 g, 8.22 mmol) is added. The mixture is stirred at room temperature overnight. After that time, solvent is evaporated and the residue is diluted with methanol and purified using a 50 g SCX cartridge and then by normal phase Isco chromatography eluting with dichloromethane and methanol to give 1.6 g of a crude material containing a mixture of regioisomers (80:20 aprox). This residue is further purified by reverse phase HPLC to give 927 mg of 2-[4-[(2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine]- r-yl)methyl]-3-methyl-pyrazol-l-yl]-3-fluoro-benzonitrile as the major regioisomer. MS (m/z): 493 (M+l).

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

Related Products of 112758-40-4,Some common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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: To a solution of Example 13 (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C5H6N2O

To a solution of 3 -methyl- lH-pyrazole-4-carbaldehyde (1 g, 9.08 mmol) in acetonitrile (10 mL) is added potassium carbonate (1.76 g, 12.71 mmol) and 2,3- difluornitrobenzene (1.73 g, 10.90 mmol) and the mixture is stirred at room temperature overnight. Water is added and the organic phase is extracted with ethyl acetate. Organic layer is dried over sodium sulfate and the solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate/hexane (20-80%) to give a 62% yield of a mixture of regioisomers containing the title compound as major product that is used with no further purification. NMR is consistent with desired structure, although mixture of regiosomers is detected: NMR (MeOD): 9.98 (s, 1H), 8.65 (d, 1H, J= 1.6 Hz), 7.99-7.26 (m, 3H), 2.49 (s, 3H). A mixture of l-(2-fluoro-6-nitro-phenyl)-3 -methyl- lH-pyrazole-4-carbaldehyde (620 mg; 2.49 mmol) (as major compound in a mixture of regioisomers in the pyrazole) and Iron (1.40 g) in ethanol (5.1 mL) and water (5.1 mL) with few drops of acetic acid is heated at 90C for 2h. After that time, it is filtered over celite, and eluted with more ethanol. Mixture is concentrated under vacuum, basified with sodium bicarbonate (saturated aqueous solution) and extracted with dichloromethane. Organic layer is decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure to give 500 mg of the title compound, as major product in a mixture of regioisomers in the pyrazole, that is used without further purification. MS (m/z): 220 (M+l). To a solution of l-(2-amino-6-fluoro-phenyl)-3-methyl-lH-pyrazole-4- carbaldehyde (500 mg, 2.28 mmol) (as major compound in a mixture of regioisomers in the pyrazole) in dichloromethane (15.21 mL), pyridine (553.31 muKappa) is added. Then, methyl chloroformate (194.17 mu) is added dropwise at 0C and the mixture is stirred at room temperature for 30 min. Water is added and the mixture is extracted with dichloromethane. Organic layer is decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate and hexane to give 418 mg of the title compound. MS (m/z): 278 (M+l). To a solution of methyl N-[3-fluoro-2-(4-formyl-3-methyl-pyrazol-l- yl)phenyl]carbamate (335 mg, 1.2 mmol) (as major compound in a mixture of regioisomers in the pyrazole) in tetrahydrofuran (6 mL) under nitrogen atmosphere and cooled to 0C, sodium hydride (60% in mineral oil) (58.3 mg) is added. Then, methyl iodide (0.4 mL) is added and the reaction mixture is stirred at 0C for 1 hour. After that time, water is added and the mixture is extracted with ethyl acetate. Organic layer is decanted, dried over sodium sulfate and solvent evaporated. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate and hexane to give 287 mg of the title compound, as major product in a mixture of regioisomers in the pyrazole, that is used without further purification. MS (m/z): 292 (M+l).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.

Reference of 112758-40-4, These common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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 mixture of 3 -methyl- lH-pyrazole-4-carbaldehyde (5 g, 45.41 mmol), potassium carbonate (9.41 g, 68.11 mmol), 2,3-difluorobenzonitrile (6.06 mL, 54.5 mmol) and dimethylformamide (50 mL) is stirred at 100C for 5 hr. and then at room temperature overnight. Water is added and a precipitated is formed. The precipitate is filtered. The aqueous solution filtered is extracted in ethyl acetate. Organic layer is washed with brine, dried over magnesium sulfate and solvent is evaporated. Both the solid precipitated and the solid recovered from organic layer after evaporation are combined and 10.4 g of the title compound is obtained and used with no further purification (the title compound is contaminated with the other pyrazole regioisomer in a ratio 90: 10). MS (m/z): 230 (M+l).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.