pyrazoles-derivatives

4522-35-4,Some common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, 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.

To a solution of 3-iodo-1H-pyrazole (10 g, 51.55 mmol, 1 eq) in DMF (100 mL) was added NaHMDS (1 M, 61.86 mL, 1.2 eq) at 0 C. The reaction mixture was stirred at 0 C for 0.5 hours. Then a solution of 2-iodopropane (10.52 g, 61.86 mmol, 1.2 eq) in DMF (20 mL) was added dropwise to the above mixture. The reaction mixture was warmed to 25 C and stirred for 12 hours. The reaction mixture was quenched with water (100 mL) and extracted EtOAc (3 ¡Á 80 mL). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate 1:0 to 50:1) to give the title compound (6.9 g, 56% yield) as a yellow oil.1H NMR (400 MHz, CDCl3): d 7.26 (d, 1 H), 6.40 (d, 1 H), 4.56-4.48 (m, 1 H) and 1.50 (d, 6 H).

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

20154-03-4, 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 20154-03-4 as follows.

Example 104: Preparation of (S)-3-methyl-2-(8-(3-(trifluoromethyl)-lH- pyrazol-l-yl)dibenzo[b,d]furan-3-sulfonamido)butanoic acidStep 1 : Preparation of (SWert-butyl 3-methyl-2-(8-(3-(trifluoromethvO-lH-pyrazol- l-yDdibenzo[b,d1furan-3-ylsulfonamido)butanoate[0234] (S)-Tert-butyl 2-(8-bromodibenzo[b,d]furan-3-sulfonamido)-3- methylbutanoate from (Example 103, Step 2, 485 mg, 1 mmol), 3- (trifluoromethyl)pyrazole (274 mg, 2 mmol), /roem’-N,N’-dimethyl-l,2- cyclohexanediamine (29 mg, 0.2 mmol), copper (I) iodide (CuI, 10 mg, 0.05 mmol), and K3PO4 (450 mg, 21 mmol) were mixed in 2 mL of toluene. The mixture was irradiated with microwave at 13O0C for 3 hours. The reaction mixture was purified by a preparative etaPLC to give 313 mg of (S)-/erf-butyl 3-methyl-2-(8-(3- (trifluoromethyl)-l/7-pyrazol-l-yl)dibenzo[b,d]furan-3-ylsulfonamido)butanoate as a white solid in 58percent yield.

According to the analysis of related databases, 3-(Trifluoromethyl)-1H-pyrazole, the application of this compound in the production field has become more and more popular.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 39806-90-1

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

1125-29-7, 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. 1125-29-7 name is 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid, 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.

Example 102 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid {4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide A mixture of 1,3,5-trimethyl-1H-pyrazole-4-carboxylic acid (71 mg, 0.46 mmol) in dichloromethane (2.5 mL) at 0 C. was treated with triphenylphosphine (145 mg, 0.55 mmol) and N-chlorosuccinimide (74 mg, 0.55 mmol). This mixture was stirred at 0 C. for 30 min and then was warmed to 25 C. for 10 min. At this time, the reaction was treated with a solution of 3-cyclopropylmethyl-1-(2-fluoro-benzyl)-8-(4-methylamino-benzyl)-3,7-dihydro-purine-2,6-dione (400 mg, 0.92 mmol) in dichloromethane (2.5 mL). The reaction was stirred at 25 C. for 24 h. At this time, the reaction was diluted with dichloromethane (50 mL) and then was washed with a saturated aqueous sodium bicarbonate solution (1*50 mL). The aqueous layer was re-extracted with dichloromethane (2*50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3:97 methanol/dichloromethane) afforded impure product. The resulting residue was purified by HPLC (15-60% acetonitrile/water (0.075% trifluoroacetic acid in both solvents) over 40 min). Fractions with the desired product were combined and concentrated in vacuo. The resulting residue was diluted with dichloromethane (50 mL) and was washed with a saturated aqueous sodium bicarbonate solution (50 mL). The water layer was re-extracted with dichloromethane (2*50 mL). The organic layers were combined and dried with magnesium sulfate, filtered and concentrated under reduced pressure. The resulting solid was dried in vacuo for 24 h to afford 1,3,5-trimethyl-1H-pyrazole-4-carboxylic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide (169 mg, 65%) as a white solid: (ES)+-HRMS m/e calcd for C31H32N7O3F (M+H)+ 570.2623, found 570.2619.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

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. 39806-90-1 name is 4-Iodo-1-methyl-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. 39806-90-1

a 1-Methyl-4-phenylethinylpyrazole To a solution of 1-methyl-4-iodopyrazole (208 g, 1 mol) and phenylacetylene (112 g, 1.1 mol) in diisopropylamine (2 l) are added, under nitrogen, copperiodide (2 g), triphenylphosphine (0.1 g) and bis-(triphenylphosphine) palladiumdichloride (0.5 g). The mixture is kept during 3 hours at ca. +35 C. and then heated for 1 hour at +90 C. The cooled reaction mixture is diluted with ethyl acetate and filtrated. Concentration of the filtrate and distillation yields the title compound: b.p. 116-118 C./0.3 mbar, m.p. 70-72 C.

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

82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

A5. General Method for the Synthesis of BOC-Protected Pyrazoles; 5-Amino-3-tert-butyl-N1-(tert-butoxycarbonyl)pyrazole; To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2¡Á300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%); mp 63-64 C.; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((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 3-Amino-5-tert-butylpyrazole, its application will become more common.

16034-46-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromoindoline (200 mg, 1.01 mmol, 1 eq) and 2-methylpyrazole-3-carboxylic acid (127.35 mg, 1.01 mmol, 1.0 eq) in EtOAc (10 mL) was added T3P (1.93 g, 3.03 mmol, 1.80 mL, 50%, 3.0 eq) and DIEA (652.54 mg, 5.05 mmol, 879.44 muL, 5.0 eq). The mixture was stirred at 60 C. for 3 h. The reaction mixture was concentrated under reduced pressure to give a residue which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 10/3, TLC: PE/EtOAc=3/1, Rf=0.42) to give the product (5-bromoindolin-1-yl)-(2-methylpyrazol-3-yl)methanone (300 mg, 960.29 mumol, 95.1% yield, 98.0% purity) as a white solid 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (s, 1H), 7.52 (d, J=2.2 Hz, 1H), 7.30-7.37 (m, 2H), 6.53 (d, J=2.0 Hz, 1H), 4.24 (t, J=8.3 Hz, 2H), 4.08 (s, 3H), 3.18 (t, J=8.3 Hz, 2H); ES-LCMS m/z 306.0, 308.0 [M+H]+.

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

7119-95-1, 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 7119-95-1 as follows.

Concentrated sulphuric acid (80 ml) was added dropwise to a stirred sample of 1-nitropyrazole (20.3 g) that was cooled in an ice-bath. The resultant mixture was stirred for 16 hours and allowed to warm to ambient temperature. The mixture was poured onto ice and stirred for 20 minutes. The resultant solid was isolated and washed with water. The filtrate was neutralised by the addition of potassium carbonate and extracted with diethyl ether. The recovered solid was added to the diethyl ether solution and the resultant solution was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-80¡ãC) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. There was thus obtained 4-nitropyrazole (16 g); 1H NMR Spectrum: (DMSOd6 + CF3CO2H) 8.57 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7119-95-1, and friends who are interested can also refer to it.

28466-26-4, Name is 4-Aminopyrazole, 28466-26-4, 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.

46 mg (0.53 mmol) of 4-amino-1H-pyrazole were dissolved in 2.4 ml of DMF and stirred with 21 mg (0.5 mmol) of sodium hydride (60% in paraffin) at 23 C. for 30 minutes. 100 mg (0.18 mmol) of 5-[4-chloro-3-(trifluoromethyl)benzyl]-2-(methylsulphonyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one (Example 39A, purity 77%) were then added, and the mixture was stirred at 120 C. for 30 minutes. The mixture was then purified directly by preparative HPLC [column: Chromatorex C18 10 mum, 250¡Á30 mm; flow rate: 50 ml/min; run time: 35 min; detection: 210 nm; injection after 3 min of run time; mobile phase A: acetonitrile, mobile phase B: water; gradient: 10% A (5.00 min)?80% A (25.00 min)?95% A (25.50-30.00 min)?10% A (30.50-35.00 min)]. The product-containing fractions were combined and concentrated. The residue was re-purified by preparative thin-layer chromatography (silica gel, mobile phase dichloromethane/methanol 20:1). This gave 41 mg (53% of theory) of the title compound.

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1H-pyrazole-4-carbaldehyde (70 mg, 728 mumol) in MeCN (5 mL) was added 1-(bromomethyl)-4-chlorobenzene (149 mg, 728 mumol) and cesium carbonate (472 mg, 1.45 mmol). The mixture was stirred at r.t. for 2h. The mixture was concentrated, diluted with EA and water. The organic phase was washed with brine (10 mL x 2), dried over Na2SO4and concentrated to give 1-(4-chlorobenzyl)-1H- pyrazole-4-carbaldehyde (162 mg, 101 percent) as a white solid, which was used in the next step without further purification

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.