Category: 1031351-95-7

Synthetic Route of 1031351-95-7, 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. 1031351-95-7 name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, 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.

Step 2: To a solution of the chloro-phosphonium salt (2.9 g, 5.95 mmol) in dry THF (20 mL) at – 78 0C was added LiHMDS (6.54 mL, 6.54 mmol) and the resulting mixture stirred at -78 0C for 1 h. The mixture was then warmed up to room temperature and a solution of lH-pyrazole-5- carboxylic acid, 3-formyl-l -methyl-methyl ester (1.0 g, 5.95 mmol) in dry THF (15 mL) was added and the resulting mixture stirred for 2 h. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (2 x 40 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate 1 :0 to 9:1) afforded, two products, 5-{(Z)-2-[3-(4- fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl} -2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (400 mg) and ethyl 5-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester (2.15 g) as off white solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1031351-95-7, 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. 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 3-formyl-l-methyl-lH-pyrazole-5-carboxylate (Bellen Chem;l g, 5.95 mmol) in CH2CI2 (30 mL) at 0 C was added bis-(2-methoxyethyl)aminosulfur-trifluoride (3.29 mL, 17.8 mmol) in CH2CI2 (5 mL) dropwise via syringe pump over 40 minutes. The mixture was allowed to stir at 0 C for 20 minutes, then the ice-bath was removed, and the mixture was allowed to warm to ambient temperature. The mixture was then allowed to stir for an additional 90 minutes and was quenched by slow addition of saturated, aqueous NaHC( (25 mL) added via syringe pump over 1 hour. The mixture was diluted with CH2CI2 (15 mL), then the layers were separated, and the aqueous layer was extracted with CH2CI2 (3 x 7 mL). The combined organic fractions were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified via column chromatography (S1O2, 50% ethyl acetate/heptanes) to give the title compound (1.01 g, 5.31 mmol, 89% yield). MS (ESI+) m/z 191 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, 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. Computed Properties of C7H8N2O3

To a solution of methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate (Bellen Chem;1 g, 5.95 mmol) in CH2Cl2 (30 mL) at 0 C was added bis-(2-methoxyethyl)aminosulfur- trifluoride (3.29 mL, 17.8 mmol) in CH2Cl2 (5 mL) dropwise via syringe pump over 40 minutes. The mixture was allowed to stir at 0 C for 20 minutes, then the ice-bath was removed, and the mixture was allowed to warm to ambient temperature. The mixture was then allowed to stir for an additional 90 minutes and was quenched by slow addition of saturated, aqueous NaHCO3 (25 mL) added via syringe pump over 1 hour. The mixture was diluted with CH2Cl2 (15 mL), then the layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 × 7 mL). The combined organic fractions were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified via column chromatography (SiO2, 50% ethyl acetate/heptanes) to give the title compound (1.01 g, 5.31 mmol, 89% yield). MS (ESI+) m/z 191 (M+H)+.

The synthetic route of Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1031351-95-7, 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. 1031351-95-7 name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, 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.

Step 2: To a solution of the chloro-phosphonium salt (2.9 g, 5.95 mmol) in dry THF (20 mL) at – 78 0C was added LiHMDS (6.54 mL, 6.54 mmol) and the resulting mixture stirred at -78 0C for 1 h. The mixture was then warmed up to room temperature and a solution of lH-pyrazole-5- carboxylic acid, 3-formyl-l -methyl-methyl ester (1.0 g, 5.95 mmol) in dry THF (15 mL) was added and the resulting mixture stirred for 2 h. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (2 x 40 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate 1 :0 to 9:1) afforded, two products, 5-{(Z)-2-[3-(4- fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl} -2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (400 mg) and ethyl 5-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester (2.15 g) as off white solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1031351-95-7, The chemical industry reduces the impact on the environment during synthesis 1031351-95-7, name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

Preparation of hydroxylamine aqueous solution: Mix 3.13g hydroxylamine hydrochloride and 2.46g sodium acetate, Add 15mL water, The aqueous solution of hydroxylamine was prepared by stirring at room temperature. Dissolve 5.1 g (30 mmol) of 3-formyl-1-methyl-1H-pyrazole-5-carboxylic acid ethyl ester(I-1, R7=Me) (synthesized according to the reporting method of CN1278820) in 20 mL of THF, Add the prepared hydroxylamine aqueous solution dropwise at room temperature, and continue stirring for 2 hours after the drop . After complete reaction, THF was removed by desolvation, after adding water, filtering, washing with water and drying to obtain 4.95 g of white solid.

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, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Chemical Institute Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Peng Weili; Xing Jiahua; Li Jiao; Xu Tianming; Huang Hongying; Yu Jiping; (32 pag.)CN111362931; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics