Month: December 2020

39806-90-1, 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 39806-90-1 as follows.

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

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.

5334-40-7, 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 4-nitro-1H-Pyrazole-3-carboxylic acid methyl ester A 20 L reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-1H-pyrazole-3-carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 C., thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 C. overnight, after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 C., the residue treated with toluene and re-concentrated (3*2.250 L, 3*2 vol) under reduced pressure at 40 to 45 C. to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5%).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

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 5334-40-7 as follows. 5334-40-7

A 2OL reaction vessel equipped with a digital thermometer and stirrer was charged with A- nitro-1H-pyrazole-3-carboxylic acid (1.117Kg, 7.11mol, 1wt) and methanol (8.950L, deltavol). The reaction mixture was stirred under nitrogen, cooled to 0 to 50C, thionyl chloride (0.581 L, delta.Omol, 0.52vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22C overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 450C, the residue treated with toluene and re-concentrated (3x 2.250L, 3x 2vol) under reduced pressure at 40 to 450C to give 4-nitro-1 /-/-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210Kg, 99.5%th).4-Nitro-1H-pyrazole-3-carboxylic acid (1.00kg, 6.37mol, 1.0wt) and methanol (8.00L, delta.Ovol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0 to 5C under nitrogen and thionyl chloride (0.52L, 7.12mol, 0.52vol) was added at this temperature. The mixture was warmed to 15 to 25C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6- DMSO). The mixture was concentrated under vacuum at 35 to 45C. Toluene (2.00L, 2.0vol) was charged to the residue and removed under vacuum at 35 to 450C. The azeotrope was repeated twice using toluene (2.00L, 2.0vol) to give 4-nitro-1 H-pyrazole-3- carboxylic acid methyl ester (1.071 Kg, 98.3%) as an off white solid.Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in MeOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1 H-pyrazole-3-carboxylic acid methyl ester as a white solid.1H NMR (400 MHz, DMSO-d6) delta 14.4 (s, 1 H), 8.9 (s, 1 H), 3.9 (s, 3H)4-Nitro-1H-pyrazole-3-carboxylic acid (1.350Kg, 8.59 MoI, 1.0 wt) and methanol (10.80L, 8.0 vol) were charged to a flange flask equipped with a mechanical stirrer, condenser and thermometer. The suspension was cooled to O to 50C under nitrogen and thionyl chloride (0.702L, 9.62 MoI, 0.52 vol) added at this temperature. The mixture was warmed to 15 to 25C over 16 to 24 hours. Reaction completion was determined by 1H NMR analysis (d6- DMSO). The mixture was concentrated under vacuum at 35 to 45C and toluene (2.70L, 2.0 vol) charged to the residue and removed under vacuum at 35 to 45C. The toluene azeotrope was repeated twice using toluene (2.70L, 2.0 vol) to give 4-nitro-1 H-pyrazole-3- carboxylic acid methyl ester [1.467Kg, 99.8%th, 108.7% w/w, 1H NMR (d6-DMSO) concordant with structure, no entrained solvent] as an off-white solid.

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

1134-50-5, The chemical industry reduces the impact on the environment during synthesis 1134-50-5, name is 1-Phenyl-1H-pyrazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

General procedure: Example 1-103 1-Phenyl-1H-pyrazole-4-carboxylic acid [7-fluoro-1-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-3-ylmethyl]-amide A mixture of 3-(aminomethyl)-7-fluoro-1-(2-fluorophenyl)quinolin-4(1H)-one (intermediate H) (50 mg, 0.175 mmol), 1 -phenyl- 1H-pyrazole-4-carboxylic acid (66 mg, 0.349 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (112 mg, 0.24 mmol), triethylamine (53 mg, 0.524 mmol), and DMF (3 mL) was stirred at room temperature overnight. The crude material was purified by flash chromatography (12 g silica gel eluting with 100% hexanes ramped to 70% ethyl acetate in hexanes). The product 1 -phenyl- 1H-pyrazole-4-carboxylic acid [7-fluoro-1-(2-fiuoro-phenyl)-4-oxo-1,4- dihydro-quinolin-3-ylmethyl]-amide (46 mg, 58%) was obtained as an off-white solid. MS calcd. for C22H14CIF2N3O2 [(M+H)+] 426.1, obsd. 426.1.

The chemical industry reduces the impact on the environment during synthesis 1-Phenyl-1H-pyrazole-4-carboxylic acid. I believe this compound will play a more active role in future production and life.

31037-02-2, These common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-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.

Preparation of ethyl 5- Fbis(tert-butoxycarbonyl)aminol-l -methyl- lH-pyrazole-4-carboxylateEthyl S-amino-l-methyl-lH-pyrazole^-carboxylate (4.7 g, 27.78) in dichloromethane (100 mL) was stirred under nitrogen in a 500 mL flask as di-tert-butyl dicarbonate (7.88 g, 36.11 mmol) was added followed by N,N-dimethylpyridin-4-amine (339 mg, 2.78 mmol). The solution was stirred for 16 h. An additonal 5 g of di-tert-butyl dicarbonate was added and the solution was stirred for an additional 2 h. Very little starting material remained at this point and the solvents were evaporated to give a residue that was purified using silica gel. Products were eluted with a gradient from 0-80 % ethyl acetate in hexane to yield 8.1 g (79%) of the title pure material.1H NMR (300 MHz, CD2C12-4) ? 7.85 (s, IH), 4.25 (q, 2H), 2.68 (s, 3H), 1.40 (s, 18H), 1.30 (t, 3H); ES-MS m/z 370.0 [M+H]+, LCMS RT (min) 3.17.

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 31037-02-2.

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 14521-80-3 as follows. 14521-80-3

Production Example 60A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.19 g of 3-bromopyrazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.31 g of 2-[3-(3- bromopyrazole-l-yl)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 59”).Active compound 591H-NMR (CDC13) 6: 8.92 (s, IH), 8.89 (d, J=5.1 Hz, IH), 8.16 (d, J=5.1 Hz, IH), 8.08-8.07 (m, IH), 7.69 (dd, J=8.8, 1.2 Hz, IH), 7.66 (d, J=2.4 Hz, IH), 7.59 (d, J=8.8 Hz, IH), 6.57 (d, J=2.4 Hz, IH)

According to the analysis of related databases, 14521-80-3, the application of this compound in the production field has become more and more popular.

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. 35277-02-2 name is 4-Fluoro-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. 35277-02-2

Sodium hydride (700 mg, 17.4 mmol, 60% dispersion in mineral oil was added to a solution of fluoropyrazole (1000 mg, 11.6 mmol) in DMF (7 mL) at room temperature. The mixture was stirred at room temperature for 40 min. The mixture was then canulated to a 1-bromo-2-chloroethane (2000 mg, 13.9 mmol, in 1 mL of DMF). The mixture was heated to 60 C. for 12 h. Water (50 mL) was added to the reaction mixture and THF (2*200 mL) was added to extract the aqueous solution. The combined organic layer was dried, filtered, and concentrated to get a waxy oil residue. LC/MS and 1H-NMR indicated it’s the mixture of two products, compound 4c and compound 4d (1000 mg, 57.4% yield).

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

120068-79-3, A common compound: 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 1; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, sodium trifluoromethylsulfinate and thionylchloride, in 6.5 molar equivalents of tolueneWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried sodium trifluoromethylsulfinate (4.29 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 13 ml. an- hydrous toluene (6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrile) under an argon atmosphere. After cooling to 00C to 5 0C with an ice bath, thionylchloride (3.57 g, 30 mmol) was added slowly while keeping the reaction temperature below 5 0C. After stirring for another 30 min, vacuum dried 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1 H-pyrazole-3- carbonitrile (8.03 g, 25 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was heated to 50 0C within 5 min by a preheated water bath. The temperature of 50 0C was kept for another 6 hours before quenching the reaction with 50 ml. of saturated NaHCO3 solution. The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separa- tion the organic layer was washed once with saturated NaHCtheta3 solution and concentrated under reduced pressure until dryness. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (8.06 g, 70 % yield, 94 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6- DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; Example 2; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, potassium trifluoromethylsulfinate and thionylchlorideWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried potassium trifluoromethylsulfinate (4.73 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), thionylchloride (3.57 g, 30 mmol), and 15 ml. anhydrous toluene under an argon atmosphere. The reaction is further conducted as described above for example 1. EPO The crude product was crystallized from refluxing chlorobenzene (100 g) affording the title compound as a white crystalline powder (7.44 g, 66 % yield, 96 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6-DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; Example 10; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, potassium trifluoromethylsulfinate and thionylchloride, in 4.5 molar equivalents of tolueneWithin a 3-neck, 50 mL round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried potassium trifluoromethylsulfinate (5.16 g, 30 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 10.4 g anhydrous toluene (4.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4- (trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrile) under an argon atmosphere. After cooling to 00C to 5 0C with external cooling, thionylchloride (3.57 g, 30 mmol) was EPO added within 15 min while keeping the reaction temperature below 5 0C. After stirring for another 30 min, vacuum dried 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1 H- pyrazole-3-carbonitrile (8.03 g, 25 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was kept at 5 0C for 60 min and then heated to 35 0C within 45 min. The temperature of 35 0C was kept for 3 hours before adding 4.6 g of toluene. After another 7 hours at 35 0C the reaction was quenched with 20 g of sodium hydroxide solution (10 wt.%).The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separation the organic layer was washed once with sodium hydroxide solution (10 wt.%). After phase separation, the organic layer was analyzed by quantitative HPLC (80.4 % yield). The crude product was crystallized from a mixture of ethylacetate and toluene affording the title compound as a white crystalline powder (7.98 g, 73 % yield, 98 % purity by quantitative HPLC).; Example 11; Sulfinylation of 5-amino-1 -[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with thionylchloride, triethylamine hydrochloride and dosage of potassium trifluoromethylsulfinateWithin a 750 mL reactor with a mechanical stirrer and a thermometer were placed vac- uum dried triethylamine hydrochloride (51.1 g, 368 mmol), 147 g anhydrous toluene(6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile), and thionylchloride (35.7 g, 294 mmol) under an argon atmosphere. After cooling to 00C to 5 0C with external cooling, vacuum dried potassium trifluoromethylsulfinate (50.4 g, 296 mmol) was added in three equal portions every 10 min while keeping the reaction temperature be…

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, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

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. 25222-43-9, name is (1H-Pyrazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., 25222-43-9

General procedure: To a mixture of 3,6-dichloropyridazine (3.73 g, 25 mmol), 4(5)-Hydroxymethylimidazole (1.96 g, 20 mmol), and Cs2CO3 (8.14 g, 25 mmol) was added acetonitrile (80 mL). The mixture was refluxed for 3 h and was poured into H2O (200 mL). 1N HCl(aq) was added slowly until the pH is ca. 7-8. Then the aqueous layer was extracted with EtOAc (150 mL) and then CH2Cl2 (100 mL x 5). The combined organic layer was dried (Na2SO4) and filtered. After removal of solvent, the product was triturated with 10percent CH2Cl2/Et2O (30 mL x 3) to give 1.74 g of product. The filtrate was concentrated and was purified by column using 60-70-80percent EtOAc/(CH2Cl2/hexane=1/1) as the eluent to give 629 mg of prouct. Total 2.36g of D (53percent) was obtained.

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.