Category: 63874-95-3

Reference of 63874-95-3, 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. 63874-95-3 name is 1-Benzyl-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.

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).

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

Reference:
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 63874-95-3, name is 1-Benzyl-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. Safety of 1-Benzyl-1H-pyrazole-4-carbaldehyde

in room temperature, 1-Benzyl-1H-pyrazole-4carboxaldehyde (18.6 g, 0.1 mol), sodium bromate (7.5 g, 0.05 mol) and 200 g of acetic acid were mixed, and 50 g of ammonia water having a molecular weight concentration of 25% of ammonia was added. 300 ml of water, heated to 90 C, the reaction is exothermic, maintain the reaction temperature of 100 C, reflux reaction for 1 hour to 1-benzyl-1H-pyrazole-4 formaldehyde complete reaction, cooled to room temperature, the reaction solution was poured into ice water After quenching and dilution, the mixture was neutralized until the reaction liquid was neutral, extracted with dichloromethane, dried, and concentrated, and then distilled under reduced pressure and recrystallized to give a product of 16.6 g, yield 91%, purity 98% or more.

The synthetic route of 1-Benzyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

63874-95-3, name is 1-Benzyl-1H-pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 63874-95-3

General procedure: Step 7. Preparation of (S)-5-chloro-4-((1-((6-(difluoromethyl)-3-fluoropyridin-2- yl)methyl)pyrrolidin-3-yl)(methyl)amino)-2-fluoro-//-(thiazol-4- yl)benzenesulfonamide formate To a solution of (S)-5-chloro-2-fluoro-4-(methyl(pyrrolidin-3-yl)amino)-//- (thiazol-4-yl)benzenesulfonamide (0.100 g, 0.234 mmol) and 6-(difluoromethyl)-3- fluoropicolinaldehyde (0.102 g, 0.585 mmol) in dichloromethane (5 ml_) was added acetic acid (0.50 ml_) and sodium triacetoxyborohydride (0.148 g, 0.702 mmol) portionwise and the resulting mixture was stirred at ambient temperature for 1 h. Concentration in vacuo and purification of the residue by preparative reverse phase HPLC, using acetonitrile in water containing 0.225% formic acid as eluent, afforded the title compound as a colorless solid (0.017 g, 13% yield): H NMR (400 MHz, CD3OD) delta 8.74 (d, J = 2.2 Hz, 1 H), 8.40 (br s, 0.8H), 7.83-7.71 (m, 3H), 7.04 (d, J = 2.2 Hz, 1 H), 7.00 (d, J = 12.0 Hz, 1 H), 6.75 (t, J = 55.2 Hz, 1 H), 4.35-4.26 (m, 1 H), 4.16-4.02 (m, 2H), 3.09-2.96 (m, 3H), 2.92-2.84 (m, 1 H), 2.83 (s, 3H), 2.22-2.12 (m, 1 H), 2.05-1.92 (m, 1 H), NH and COOH not observed; MS (ES+) m/z 549.9 (M + 1), 551.9 (M + 1).

The synthetic route of 63874-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BURFORD, Kristen, Nicole; CHOWDHURY, Sultan; COHEN, Charles, Jay; DEHNHARDT, Christoph, Martin; DEVITA, Robert, Joseph; EMPFIELD, James, Roy; FOCKEN, Thilo; GRIMWOOD, Michael, Edward; HASAN, Syed, Abid; JOHNSON, James, Philip, Jr.; ZENOVA, Alla, Yurevna; (493 pag.)WO2017/201468; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 63874-95-3, name is 1-Benzyl-1H-pyrazole-4-carbaldehyde, 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 63874-95-3, HPLC of Formula: C11H10N2O

General procedure: General procedure: To a solution of 4-formyl-1H-1-tritylprazole (8a) (94.6 mg, 0.28 mmol) inCH2Cl2 (6 mL) was added 70% mCPBA (131.8 mg, 0.53 mmol) at 0 C, with stirring. After 5 h,saturated NaHCO3 aq (10 mL) was added to quench the reaction mixture. The mixture was extractedwith CH2Cl2 3 times. Combined organic layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude formate. To an acetone solution of the crude formate (6 mL),20% NaOH aq (4 mL) was added, then the mixture was heated under reflux for 1 h, then crotyl bromide(48 L, 0.42 mmol) was added to the cooled mixture. After stirring for 3 h, saturated NH4Cl aq wasadded to the reaction mixture to quench, the mixture was condensed under reduced pressure, extractedwith CH2Cl2 for 3 times. The combined CH2Cl2 layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude residue, which was purified with flash column chromatography(EtOAc:Hexane = 1:10) to give 4-(2-butenyl)oxy-1H-1-tritylpyrazole (1e) (54.5 mg, 51%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.