Category: 25016-11-9

25016-11-9, Name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 25016-11-9, 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.

Preparation Example 6 N-[3-(4-t-Butylphenyl)-2-methylpropyl]-N,1-dimethyl-1H-pyrazol-4-ylmethylamine (I-17) Route B-2: After suspending 200 mg (3.2 mmol) of sodium cyanoborohydride in 2 ml of absolute methanol, 380 mg (1.7 mmol) of 3-(4-t-butylphenyl)-N,2-dimethylpropylamine (IV-1) was added thereto. Subsequently, to this was added a solution of 170 mg (1.6 mmol) 4-formyl-1-methylpyrazole/2 ml absolute methanol by portions, the pH was adjusted to 7 with acetic acid, and then stirring was conducted at room temperature for 8 h. Methanol was removed under reduced pressure, water was added and extraction with ethyl acetate was done. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified with a silica gel (Silica gel 60, 230-400 mesh, Merck Co.) column (eluent composition: n-Hex/AcOEt=1/1) to afford 340 mg of the desired compound (I-17) as an oil. The yield was 70.1%.

Statistics shows that 1-Methyl-1H-pyrazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 25016-11-9.

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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., 25016-11-9

D8: (?)-3-(l-Methyl-lH-pyrazol-4-yl)acrylic acidA mixture of l-methyl-lH-pyrazole-4-carbaldehyde (13 g, 118 mmol), malonic acid (12.29 g, 118 mmol), pyridine (65 ml) and piperidine (0.234 ml, 2.361 mmol) was heated to 110 C under argon for 4h. After cooling, water(lOOml) was added, followed by aqueous ammonia (12ml) to obtain a clear solution, which was acidified to pH ~ 1 with hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to obtain the title compound (7.5 g, 40.5 % yield). LCMS: rt =0.92 min, [M+H+] =153

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.

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 25016-11-9 as follows. 25016-11-9

1-Methyl-1H-pyrazole-4-carbaldehyde (CAS : [25016-11-9 ]) (100 mg, 0.9 mmol) was added dropwise at 20 C, to a solution of intermediate 9 (300 mg, 0.9 mmol) and Et3N (0.23 mL, 1.64 mmol) in MeOH (5 mL). The mixture was stirred at rt for 4 h. The mixture was cooled to 0 C then NaBH4 (47 mg, 1.23 mmol) was added portionwise and the mixture was stirred at rt for 15 h. The mixture was poured into ice water containing NH4Cl 10%, and extracted with DCM three times. The organic layers were gathered, washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 24g GRACE, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 140 mg (yield 40%) of compound 11.

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

These common heterocyclic compound, 25016-11-9, name is 1-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. 25016-11-9

General procedure: To a solution of S2 (50 mg, 0.2 mmol) in 1,2-dichloroethane (DCE, 1 mL) was added aldehyde(1.1 equiv), sodium triacetoxyborohydride (79 mg, 0.5 mmol) and AcOH (25 muL, 0.5 mmol) at roomtemperature. The solution was stirred for 16 h and concentrated. The solution was extracted withethyl acetate (3 mL), washed with citric acid solution, saturated NaHCO3, and concentrated. Theremaining residue was dissolved in THF and chloroacetyl chloride (23.8 muL, 0.3 mmol) was thenadded at 0 C. The solution was warmed to room temperature and stirred for 2 h. The solutionwas concentrated and separated by preparative TLC to afford RS004 analogues.

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 25016-11-9.

25016-11-9, 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. 25016-11-9 name is 1-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 intermediate 10b (200 mg), 1-methyl-i H-pyrazole-4-carboxaldehyde (183 mg; 1.66 mmol) and AcOH (32 jiL; 0.555 mmol) in DCE (6 mL) was stirred at 50Cfor 2 hours. The reaction mixture was cooled to room temperature and NaBH(OAc)3 (353 mg; 1.665 mmol) was added. The reaction mixture was stirred at room temperature overnight, poured onto a 10% aqueous solution of K2C03 and extracted with DCM. The organic layer was decanted, dried over MgSO4, filtered and evaporated to dryness. The residue was purifed by chromatography over silica gel (irregular SiOH,24g; mobile phase: gradient from 0% NH4OH, 0% MeOH, 100% DCM to 1% NH4OH,10% MeOH, 90% DCM). The pure fractions were collected and evaporated to dryness yielding 165 mg of compound 28 as an oil (73%). Compound 28 was dissolved in ACN and HC1 (4N in dioxane) (277 jiL; 1.11 mmol) was added. The HC1 salt was filtered but revealed to be too hydroscopic. The residue was then dissolved inDCM/MeOH and the organic layer was washed with a 10% aqueous solution of K2C03, dried over MgSO4, filtered and evaporated to dryness. The resulting residue was dissolved in ACN and fumaric acid (47 mg; 0.404 mmol; 1 eq) was added and the solution was allowed to stand until crystallization (overnight). The precipitate was filtered, washed with ACN then Et20 and dried yielding 188 mg of compound 28 as thefumarate salt (1 equivalent based on 1H NMR).

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

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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., 25016-11-9

103a) (E)-tert-Butyl 3-(1 -methyl-1 H-pyrazol-4-yl)acrylate To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (12.60 g, 49.9 mmol) in tetrahydrofuran (THF) (30 mL) was added NaH 60% dispersion in mineral oil (2.179 g, 54.5 mmol) slowly. The mixture was stirred for 10 min at room temperature. A solution of 1 -methyl-1 H-pyrazole-4-carbaldehyde (5.0 g, 45.4 mmol) in tetrahydrofuran (THF) (30 mL) was added slowly. After addition, the reaction mixture was stirred for 20 min at room temperature. The LCMS showed a complete reaction. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous MgSCv It was filtered and the filtrate was concentrated to give the crude product which was then purified on the Combiflash column chromatography eluting with a gradient of 0 to 50% ethyl acetate in hexanes. The title compound was obtained as clear colorless oil (9.0 g, 43.2 mmol, 95 % yield). LC-MS m/z 208.9 (M+H)+, 0.93 min (ret. time).

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.