Category: pyrazoles-derivatives

Electric Literature of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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.

1-(ethoxyethyl)-4-iodo-1H-pyrazole (20).; A 22 L 4-neck flask equipped with an mechanical stirrer, thermowell, N2 inlet and condenser was charged with 4-iodo-1H-pyrazole (14, 1.00 Kg, 5.16 mol) and toluene (10 L) and ethyl vinyl ether (18, 557 g, 740 mL, 7.73 mol, 1.5 equiv) was added. To the suspension 4 M HCl in dioxane (32 mL, 0.128 mol, 0.025 equiv) was added over 5 min with formation of a slightly thicker white suspension. The mixture was heated carefully to 35-40 C. at which point a mild exotherm to about 40 C. occurred with rapid dissolution of all solids to give a clear light yellow solution. The reaction mixture was heated at about 40 C. for an additional 0.5 hr until the GC analysis indicated the reaction was complete. The solution was allowed to cool to 25-30 C. and solid NaHCO3 (108 g, 1.29 mol, 0.25 equiv) was added. The suspension was stirred for 1 hr at room temperature to ensure the complete neutralization of HCl. The mixture was then filtered and the filtrate was concentrated under reduced pressure. The residual liquid was fractionally distilled to afford 1-(ethoxyethyl)-4-iodo-1H-pyrazole (20, 1.346 Kg, 1.373 Kg theoretical, 98%) as a pale yellow liquid (bp 89-93 at about 1 torr). For 20: 1H NMR (CDCl3, 250 MHz) delta ppm 7.61 (s, 1H), 7.47 (s, 1H), 5.46 (q, 1H, J=6.0 Hz), 3.48-3.23 (m, 2H), 1.60 (d, 3H, J=6.0 Hz), 1.11 (t, 3H, J=7.0 Hz); C7H11IN2O (MW, 266.08), LCMS (EI) m/e 267 (M++H).

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

2458-26-6, name is 3-Phenyl-1H-pyrazole, 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. Formula: C9H8N2

General procedure: A mixture of acetophenone and dimethylformamide dimethylacetal (2.0 equiv.) was refluxed overnight. The reaction mixture was allowed to cool down to room temperature and was concentrated under reduced pressure. The remaining residue was suspended in hexanes and filtered. The filter cake was washed with plenty of hexanes. (E)- 3-(dimethylamino)-l- phenylprop-2-en-l-one was obtained. (0260) Hydrazine-monohydrate (5.0 equiv.) was added to a solution of (E)- 3- (dimethylamino)-l-phenylprop-2-en-l-one in EtOH and the resulting reaction mixture was refluxed for 2 hours. The reaction was then allowed to cool down to room temperature and was concentrated under reduced pressure. The remaining residue was diluted with H2O and extracted with CH2CI2. The organic phase was dried over MgS04, filtered and concentrated under reduced pressure. The residue was considered pure enough by -NuMuKappa (>95%) to be used without further purification. (0261) A mixture of phenylpyrazole, iodoarene (1.0 equiv.), copper iodide (20 mol%), trans- (0262) 1,2-diaminocyclohexane (25 mol%), potassium carbonate (2.0 equiv.) in dioxane was stirred at 100C under argon for 16 hours. After cooling down to room temperature, the reaction mixture was diluted with H2O and extracted with EtOAC. The gathered organic phases were washed with NH4CI/NH3 (v/v : 1/1), brine, dried over MgSC , filtered and concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel (Hexanes/EtOAc).

The synthetic route of 2458-26-6 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 15953-45-4, These common heterocyclic compound, 15953-45-4, name is 5-Chloro-3-methyl-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.

(b) 5-Chloropyrazole-3-carboxylic acid..A mixture of 5-chloro-3-methylpyrazole (3.6 mmol; see step (a) above), water (6 mL) and terf-butanol (1.2 mL) was heated to 750C, after which KMnO4 (1.42 g, 9 mmol) was added. The mixture was stirred at 75C overnight and filtered hot. The solids were washed with boiling water. The combined cooled filtrates were extracted with EtOAc, and the combined extracts washed with NaCI (sat., aq.), dried (MgSO4) and concentrated. The crude solid was recrystallised from EtOAc/hexane/pentane to give the sub-title compound as white crystals (Yield: 350 mg (67%)). 1H-NMR (DMSO-d6, 400 MHz), delta 13.65 (br s, 1 H), 6.80 (s, 1 H). (d) 5-Chloropyrazole-3-carboxylic acid. A solution of KMnO4 (3.5 g, 22 mmol) in water (120 mL) was added in portions over a period of 5 h at 700C to a solution of 5-chloro-3-methylpyrazole (1.0 g, 8.8 mmol; see step (c) above) in water (50 mL) and terf-butanol (1 mL). The mixture was stirred at 7O0C overnight and filtered through Celite. The colourless filtrate was concentrated and acidified with HCI (aq., 2M). Filtration gave the title compound as a white powder which was used without further purification. (Yield: 913 mg, 80%). 1H-NMR (DMSO-d6): delta 6.80 (s, 1 H), 4.40 (br s, 1 H).

Statistics shows that 5-Chloro-3-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 15953-45-4.

Electric Literature of 49633-25-2, 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 49633-25-2 as follows.

[00754] Intermediate 80a: benzyl 2-(3-isopropylpyrazol-1 -yI)acetate[00755] 5-lsopropyl-1H-pyrazole (1 00mg, 0.91 mmol) and potassium carbonate (376mg, 2.72mmol) was left to stir in MeCN (3mL) for 30 mins before the addition of benzyl bromoacetate (0.21 mL, 1 .36mmol). The resultant mixture was heated to 60 C and left to stir at temperature overnight. The reaction was then quenched by addition of water (2OmL) and extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give benzyl 2-(3-isopropylpyrazol-1-yl)acetate (200mg, 0.77mmol, 85%) which was used inthe next step without further purification.1H NMR (CDCI3,400MHZ) O/ppm: 7.41-7.33 (6H, m), 6.18 (1H, d, J= 2.3Hz), 5.21 (2H, 5), 4.96 (2H, 5), 3.04 (1H, sept, J= 7.0Hz), 1.31 (3H, 5), 1.29 (3H, 5).MS Method 2: RT: 1.87 mi mlz 259.0 [M+H]

According to the analysis of related databases, 49633-25-2, the application of this compound in the production field has become more and more popular.

Electric Literature of 37687-24-4, A common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

Example 41; (5R, 6E&Z)-7-oxo-6- (4H, 10H-pyrazolo [5, 1-c] [1, 4] benzoxazepin-2-ylmethylene)-4- thia-1-azabicyclo [3. 2. 0] hept-2-ene-2-carboxylic acid, sodium salt Step 1: Preparation of 1-(2-fluorobenzyl)-1H-pyrazole-3,5-dicarboxylate 2-fluorobenzyl bromide (2.0 ml, 16.58 mmol) was added to a mixture of diethyl 3,5- pyrazoledicarboxylate (3.01 g, 14.18 mmol), Cs2CO3 (5.57 g, 17.1 mmol), and acetonitrile (140 ml) under N2. Heated to 60C for two hours and then cooled to room temperature. Filtered and concentrated the reaction solution. Added water (-200mL) to the resulting residue and extracted with EtOAc. Washed organics with water and brine. Dried organics over sodium sulfate and filtered and concentrated. Obtained diethyl 1- (2- fluorobenzyl)-1 H-pyrazole-3, 5-dicarboxylate (light-yellow oil) in quantitative yield.

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Application of 149739-65-1, The chemical industry reduces the impact on the environment during synthesis 149739-65-1, name is 3-(3-Bromophenyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Synthesis of intermediate compound 4[00107] In a 300 ml eggplant-type flask, 7.00 g (31.4 mmol) of compound 3, 3.30 g (34.5 mmol) of sodium tert-butoxide, and 100 ml of DMF were placed. Then, 2.15 ml (34.5 mmol) of idomethane was added dropwise to the resultant mixture, followed by stirring at room temperature for 24 hours. The loss of the raw materials and production of a new compound were confirmed by TLC (Thin Layer Chromatography) . The reaction solution was concentrated, and an organic phase was recovered by three times of separation with toluene/water. The organic phase was dried over magnesium sulfate,concentrated, and then purified by silica gel columnchromatography (developing solvent toluene : heptane : ethyl acetate = 10:10:1). A target substance was concentrated to produce 5.21 g (22.0 mmol) of compound 4 (yield 70.0%).Nine protons were attributed by 1H-NMR (CDC13: 7.95 (s, 1H) , 7.71 ppm (d, 1H) , 7.42-7.39 ppm (m, 2H) , 7.26 ppm (t, 1H) , 6.53 ppm (d, 1H) , 3.96 ppm (s, 3H) ) . A peak was observed at m/z = 236 in GS-MS (gas chromatography direct-coupled to mass spectrometry) to confirm the target compound.

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-(3-Bromophenyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Electric Literature of 1384973-12-9,Some common heterocyclic compound, 1384973-12-9, name is 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, molecular formula is C4H3BrN4, 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.

To a solution of 5-amino-3-bromo-lH-pyrazole-4-carbonitrile (500 mg, 2.67 mmol) in EtOH (5 mL)/H20 (5 mL) /toluene (5 mL) were added 3 -pyridine boronic acid (493 mg, 4.01 mmol), K3P04 (2.13 g, 8.02 mmol) and Pd(dppf)Cl2 (391 mg, 0.53 mmol) under N2. The resulting mixture was stirred at 110C for 64 hours under N2. After cooling to rt, the mixture was concentrated in vacuo, diluted with ethyl acetate, washed with water (10 mL x 3) and dried over MgS04. After filtration, the filtrate was concentrated in vacuo. The residue was purified by preparative-TLC to afford 300mg of the desired product: MS (m/z): 185.9 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, its application will become more common.

These common heterocyclic compound, 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-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. SDS of cas: 400877-57-8

A solution of l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (4.8 g, 25.94 mmol) in dry MeOH (100ml) was thoroughly purged with argon, treated with 10% Pd-C (2.7 g, 2.59 mmol), and again purged with argon. Then the reaction mixture was hydrogenated under a balloon pressure of hydrogen at rt for overnight. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated and dried to give the title compound as gray-white solid (3.4 g, 84%), which was used in the next reaction step without further purification.

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

Adding a certain compound to certain chemical reactions, such as: 16034-48-3, name is 1-Pyrazoleacetic Acid, 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 16034-48-3, SDS of cas: 16034-48-3

To a solution of 1 .76 g of Pyrazol-1 -yl-acetic acid in 20 ml of dry DMF 2.09 g of HOAT, 3.75 g of EDC and 6.9 ml of DIPEA were added at 0C. After 30 min 3.3 g of 3-amino-4-(1 -ethyl-propylamino)-benzoic acid methyl ester were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by precipitation from heptane to yield 2.28 g (47 %) of 4-(1 -Ethyl-propylamino)-3-(2- pyrazol-1 -yl-acetylamino)-benzoic acid methyl ester. C 8H24N4O3 (344.42), LCMS (method 8_1_1 ): Rt = 0.85 min, m/z= 345.15 [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, 1-Pyrazoleacetic Acid, other downstream synthetic routes, hurry up and to see.

Related Products of 6825-71-4, A common heterocyclic compound, 6825-71-4, name is Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate, molecular formula is C6H10N4O2, 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.

To a solution of sodium ethoxide in EtOH (0.49 N, 100 mL) were added ethyl 3,5- diamino-lH-pyrazole-4-carboxylate (2.08g, 0.012 mol), followed by solid 1,3-dimethyluracil (1.7 g, 0.012mol) and then the reaction mixture was stirred overnight at 90 C. The reaction mixture was cooled to r.t, filtered to give the title compound as a pink solid (2.1 g, 79%). NMR (300MHz, OMSO-de): delta (ppm) 11.30 (brs, 1H), 8.23 (d, J= 7.86 Hz, 1H), 5.93 (brs, 2H), 5.89 (d, J= 7.83 Hz, 1H), 4.26 (q, J= 7.08 Hz, 2H), 1.28 (t, J= 7.08 Hz, 3H).

The synthetic route of 6825-71-4 has been constantly updated, and we look forward to future research findings.