pyrazoles-derivatives

Electric Literature of 575452-22-1, 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. 575452-22-1 name is 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, 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 dry tetrahydrofurane (for 0.019 mol of starting material 40 mL of tetrahydrofurane was used),2.5 M n-BuLi solution in n-hexane (1.1 equiv.) was added dropwise under argon atmosphere at -78C temperature, following by addition of diisopropylamine (1.2 equiv.) at -78 C degree and left tostir at same temperature for 30 min. Then pyrazole 2a, 3a or 5a (1 equiv.) solution intetrahydrofurane (for 0,019 mol of protected pyrazole – 5 mL of THF were used) was added to thereaction mixture at -78 C temperature and left to stir at the same temperature for additional 30 min.Then dimethylformamide (1.3 equiv.) solution in tetrahydrofurane (for 0.025 mol ofdimethylformamide – 5 mL of THF were used) were added dropwise at -78 C degree and left towarm to room temperature overnight. Reaction mixture was cooled down to 5 C temperature andquenched with saturated NH4Cl solution in deionized water (for 0.019 mol of starting material – 12mL of saturated NH4Cl solution were used). Organic layer was separated, inorganic layer wasextracted with dichloromethane (3×10 mL). Organic layers were combined and washed withdeionized water (2×10 mL), dried with anhydrous Na2SO4 and evaporated under reduced pressure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, 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. 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., SDS of cas: 18213-75-7

To 5 -amino- 1 -methyl- lH-pyrazole-4-carboxamide (2 g, 14.3 mmol) and sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate (3.64 g, 17.12 mmol) was added trimethylsilyl polyphosphate (20 mL) and the mixture was heated at 130 C overnight. The solution was cooled, equal volumes of EtOAc and water were added, and the mixture was stirred for 30 min. The organic layer was washed with brine, separated, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was dissolved in DCM and extracted with 1 N aqueous NaOH. The aqueous layer was washed with DCM and then acidified with 4 N HC1 and extracted with EtOAc. The organic layer was separated, dried over Na2S04, filtered, and concentrated under reduced pressure to afford 6-(difluoro(5-fluoropyridin-2- yl)methyl)-l -methyl- lH-pyrazolo[3,4-d]pyrimidin-4-ol (1.85 g, 44%) as a solid, which was used without further purification. H NMR (300 MHz, DMSO-t 6) delta 11.67 (s, 1H), 8.77 (s, 1H), 7.95 – 8.21 (m, 3H), 3.74 (s, 3H).

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.

Synthetic Route of 1572-10-7, 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. 1572-10-7 name is 3-Amino-5-phenylpyrazole, 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: The compound tetronic acid (15) (80 mg, 0.8 mmol) was dissolved in 4 mL of ethanol, followed by addition of terphenyl aldehyde 13a (221.2 mg, 0.8 mmol) and 3-amino-5-phenyl pyrazole 14a (127.2 mg, 0.8 mmol). The reaction mixture was refluxed in ethanol at 78 C for an hour. Then reaction suspension was cooled to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL), then recrystallized from ethanol to afford pure compound 8a as a white solid, 340 mg in 85% yield. Mp: 273-274 C; 1H NMR (300 MHz, DMSO-d6): delta 4.80 (s, 2H), 5.25 (s, 1H ), 6.89-6.99 (m, 1H), 7.19-7.35 (m, 7H), 7.42-7.52 (m, 4H), 7.65 (dd, 4H, J = 8.8, 11.7 Hz), 8.05 (s, 1H), 10.19 (s, 1H ), 12.56 (s, 1H); 13C NMR (300 MHz, DMSO-d6): delta 30.5, 64.8, 94.4, 99.8, 111.1, 111.3, 113.2, 121.3, 125.4, 126.1, 126.7, 126.9, 127.1, 127.2, 127.3, 128.3, 128.7, 128.8, 132.7, 137, 137.2, 138.8, 139.3, 145.8, 152.7, 157.7, 172.2; MS (ESI): 500 [M+H]+; HRMS (ESI) calcd for C32H23O2N3F [M+H]+ 500.1712; found: 500.1738.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-5-phenylpyrazole, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, 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 52222-73-8, Computed Properties of C4H3F3N2

Example 29 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-4-[4-(trifluoromethyl)-1H-pyrazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Under argon atmosphere, 200 mg (purity 62%, 0.24 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was suspended in 2.5 ml of absolute acetonitrile, and 656 mg (4.82 mmol) of 4-(trifluoromethyl)-1H-pyrazole, 157 mg (0.48 mmol) of caesium carbonate, 7 mg (0.05 mmol) of copper(I) oxide and 26 mg (0.19 mmol) of 2-hydroxybenzaldehyde-oxime were added. The mixture was heated in the microwave for 1 h at 200 C. The reaction solution was filtered and purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80?100:0). 85 mg (63% of theor.) of the target compound was obtained. LC-MS (method 1): Rt=1.33 min; MS (ESIpos): m/z=523 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.56 (s, 6H), 5.91 (s, 2H), 7.15 (t, 1H), 7.20-7.25 (m, 2H), 7.34-7.39 (m, 1H), 7.52 (dd, 1H), 8.51 (s, 1H), 8.71 (dd, 1H), 8.92 (dd, 1H), 9.30 (s, 1H), 11.99 (s, 1H).

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 34605-66-8 as follows. Recommanded Product: 34605-66-8

To a solution of 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole (6.4 g) in tetrahydrofuran (70 mL) was added dropwise n-butyllithium (1.6 M hexane solution, 27 mL) at -78 C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added dropwise di-tert-butyl dicarbonate (11 mL) at -78 C., and the mixture was stirred for 2 hr while gradually raising the temperature to room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.9 g). 1H NMR (400 MHz, DMSO-d6) delta1.56 (9H, s), 1.94-2.13 (6H, m), 4.09 (3H, s), 5.77 (2H, s), 6.84 (1H, s). MS(ESI+): [M+H]+ 276.1.

According to the analysis of related databases, 34605-66-8, the application of this compound in the production field has become more and more popular.

These common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, 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. Recommanded Product: 3994-50-1

To a solution of tert-butyl N- [(15)-i -(5 -bromopyridin-3 -yl)but-3 -en- l-yl]carbamate (1.0 g, 3.06 mmol), prepared as described in Intermediate 26, in dioxane (10ml) was added 1-methyl-4-nitro-1H-pyrazole (0.427 g, 3.36 mmol), di(adamantan-1-yl)(butyl)phosphine (0.164 g, 0.458 mmol), K2C03 (1.267 g, 9.17 mmol) and pivalic acid(0.106 ml, 0.917 mmol). The reaction mixture was purged with Ar. Pd(OAc)2 (0.069 g,0.306 mmol) was added and the solution was stirred at 100 C. After 4 h, the reactionwas quenched with water (20 ml) and extracted with EtOAc (3 x 50 ml). The combinedorganic layers were washed with brine (20 ml), dried (MgSO4), filtered, and concentrated.The residue was purified by normal phase chromatography using heptanes and EtOAc aseluents to give tert-butyl N-[( 15)-i -[5 -(1 -methyl-4-nitro- 1 H-pyrazol-5 -yl)pyridin-3 -yl]but-3-en-i-yl]carbamate (0.85 g, 74%) as a white foam. MS(ESI) m/z: 374.5 (M+H).?H NMR (500MHz, CDC13) oe 8.74 (d, J=i .9 Hz, 1H), 8.57 (d, J=i .9 Hz, 1H), 8.25 (s,1H), 7.72 (t, J=i.9 Hz, 1H), 5.73 (ddt, J=17.i, 10.2, 7.2 Hz, 1H), 5.26 – 5.17 (m, 2H),4.99 (br. s., 1H), 4.93 – 4.84 (m, 1H), 3.80 (s, 3H), 2.75 – 2.52 (m, 2H), 1.43 (br. s., 9H).

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

These common heterocyclic compound, 103626-03-5, name is Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-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. name: Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate

Example 264 A mixture of ethyl 3-hydroxy-1-methyl-1H-pyrazole-4-carboxylate (1.93 g), 4-(4-chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole (3.89 g), potassium carbonate (3.15 g) and N,N-dimethylformamide (30 mL) was stirred overnight at 60C. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained colorless crystals were collected by filtration to give ethyl 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxylate (5.23 g, yield 97%). The crystals were recrystallized from acetone-hexane. melting point: 134-135C.

The synthetic route of Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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. SDS of cas: 3994-50-1

Pd / C (10%, 500 mg) was added to the column1-methyl-4-nitro-1H-pyrazole (1.90 g, 14.9 mmol)And methanol (25 mL)Hydrogen at room temperature overnight.Diatomaceous earth filter, dichloromethane washing filter cake,The filtrate was concentrated under reduced pressure, (Eluent: ethyl acetate / methanol (v / v) = 18/1) to give 1.35 g of a black solid, yield:83.7%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3994-50-1, its application will become more common.

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 25699-83-6 as follows. Product Details of 25699-83-6

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (15 mL). This was followed by dropwise addition of a 4-(1H-pyrazol-1-yl)benzonitrile (250 mg, 1.48 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) with stirring at 0 C. To this was added LiAlH4 (337 mg, 8.87 mmol, 6.00 equiv). The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of NaOH (15%, aq). The resulting solution was extracted with 3*50 mL of dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The product was obtained as 0.251 mg of a white crude solid.

According to the analysis of related databases, 25699-83-6, the application of this compound in the production field has become more and more popular.

Reference of 133228-21-4, The chemical industry reduces the impact on the environment during synthesis 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, I believe this compound will play a more active role in future production and life.

To a solution of N,N-dimethylsulfamoylpyrazole (44.0 g, 0.251 mol) in dry tetrahydrofuran (500 ml) at -78C was added dropwise a solution of n-butyllithium (2.5 M in hexane, 105.5 ml, 0.264 mol) while maintaining the temperature below -60C. A thick solid formed during the addition. Upon completion of the addition the reaction mixture was maintained for an additional 15 minutes, after which time a solution of 1,2-dibromotetrachloroethane (90 g, 0.276 mol) in tetrahydrofuran (150 ml) was added dropwise while maintaining the temperature below -70C. The reaction mixture turned a clear orange; stirring was continued for an additional 15 minutes. The -78C bath was removed and the reaction was quenched with water (600 ml). The reaction mixture was extracted with methylene chloride (4x), and the organic extracts were dried over magnesium sulfate and concentrated. The crude product was further purified by chromatography on silica gel using methylene chloride-hexane (50 : 50) as eluent to afford 57.04 g of the title product as clear colorless oil. 1H NMR (CDCl3): delta 3.07 (d, 6H), 6.44 (m, 1H), 7.62 (m, 1H).

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, N,N-Dimethyl-1H-pyrazole-1-sulfonamide, other downstream synthetic routes, hurry up and to see.