Day: July 1, 2021

Electric Literature of 75415-03-1, 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. 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 4a (2 mmol), NaH (2.4 mmol) and indole were dissolved in DMF (10 mL). The reaction mixture was stirred at room temperature for 12h before diluted with water (20 mL) and extracted with ethyl acetate (30 mL × 3). The organic layer was concentrated in vacuum. Purication by ash column chromatography gave the target product 5h.

The chemical industry reduces the impact on the environment during synthesis 2-(1H-Pyrazol-3-yl)pyridine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Chen-Ru; Wang, Ze-Feng; Shi, Lu; Wang, Zhong-Chang; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2382 – 2390;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1310350-99-2,Some common heterocyclic compound, 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C5H3ClF2N2O2, 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.

a) 1-Difluoromethyl-1H-pyrazole-3-carboxylic acid methyl ester A solution of 1-difluoromethyl-1H-pyrazole-3-carboxylic acid (CAS925179-02-8) (500 mg, 3.1 mmole) in methanol (18 ml) was cooled to 0 C. and treated with sulphuric acid (98%, 0.2 ml, 3.1 mmol). The mixture was heated to reflux for 2 hours, cooled to 22 C. and concentrated at reduced pressure. The residue was partitioned between AcOEt and water, the organic layer was washed with water until the water phase showed a neutral pH, dried and evaporated to give the title compound (535 mg) as a colorless liquid which was used without further purification. MS: m/z=177.1 [M+H]+.

The synthetic route of 1310350-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banner, David; Guba, Wolfgang; Hilpert, Hans; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Rogers-Evans, Mark; Rombach, Didier; Woltering, Thomas; Wostl, Wolfgang; US2011/312937; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Compound 2 (15 mmol) and SOCl2 (30 mL) were added. The mixtures were heated to reflux at 80 &176;C for 3 hours. Residual SOCl2 was removed by vacuum distillation in order to obtain compound 3. Finally, the compounds 6 (10 mmol) dissolved in dichloromethane (20 mL) and triethylamine (5 mL) were added. The mixtures were cooled to 0 &176;C and compound 3 dissolved in dichloromethane (20 mL) were added dropwise under stirring at a temperature not exceeding 5 &176;C. The final mixtures were stirred at room temperature for 3 hours and the target compounds 1a-1p were purified via column chromatography.

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 176969-34-9.

Reference:
Article; Zhang, Aigui; Zhou, Jingya; Tao, Ke; Hou, Taiping; Jin, Hong; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3042 – 3045;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-45-8, A common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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 stirred solution of 4-bromo-pyrazole (10.44 g, 71.03 mmol) in anhydrous DMF (96 mL), cooled to 0 C., was slowly added NaH (60% in mineral oil) (3.13 g, 78.133 mmol). The solution was stirred for 1 hour at 0 C. 4-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (19.82 g, 71.03 mmol) was added slowly and the reaction was heated to 100 C. overnight or until consumption of the pyrazole by NMR. The reaction was cooled to room temperature and water added (20 mL) followed by extraction with EtOAc. The combined extracts were washed with saturated aqueous NaCl (4*20 mL), dried with Na2SO4 and concentrated to afford 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as an orange oil. The oil was purified using silica gel chromatography eluding with 10% EtOAc/hexanes to 25% EtOAc/hexanes to provide 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (10.55 g, 45% yield) with a Rf=0.4 (25% EtOAc/hexanes, using iodine as the stain). 1H NMR (CDCl3, 400 MHz) delta 7.46 (s, 1H), 7.43 (s, 1H), 4.23 (m, 3H), 2.88 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.47 (s, 9H).

The synthetic route of 2075-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 181585-93-3,Some common heterocyclic compound, 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, 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 methyl 3-nitro- 1H-pyrazole-5-carboxylate (500 mg) in Ethanol (0.25M) was added 10% Palladium on Carbon (0.1 eq) and ammonium fomiate (8 eq) and the reaction was heated for 1 hour at 70C then cooled to room temperature, filtered through celite, rinsed withMethanol and concentrated to dryness. The crude intermediate was suspended in DCM and extracted with water. To the organic layer was added 3 eq of MP-TsOH catch and release resin whereupon the mixture was stirred for 1 hour, filtered to collect resin then eluted with 7N Ammonia in MeOH and concentrated to dryness to afford 100 mg of methyl 3-amino-1H-pyrazole-5-carboxylate. To a solution of methyl3-amino-1H-pyrazole-5-carboxylate in dioxane was added di-tert-butyl dicarbonate (1.5 eq) and the reaction was heated at 120C overnight, then stirred at room temperature for 6 hours before the addition of imidazole (4.5 eq). The reaction mixture was subsequently refluxed at 130C for 2 hrs then stirred at room temperature overnight, concentrated to dryness, suspended in Ethyl acetate and extracted 3x with 0.25N HC1 solution, dried, filtered and concentrated to afford 427 mg ofmethyl 3-Qert-butoxycarbonylamino)-1H-pyrazole-5-carboxylate as a light pink solid. Similar to as described in General Procedure A, 3-(tert-butoxycarbonylamino)- 1H-pyrazole-5-carboxylate (200 mg) was reacted with 2-fluoro-4-iodo-pyridine to give methyl 5-(tert-butoxycarbonylamino)- 1 -(4-iodo-2-pyridyl)pyrazole-3-carboxylate. The crude material was used directly in subsequent reactions. To a solution of5-(tertbutoxycarbonylamino)-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate in DCM was added 4NHC1 in dioxane (10 eq). The reaction was stirred at room temperature for 30 minutes thenconcentrated to dryness to afford crude methyl5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate as the HC1 salt. Similar to as described inGeneral Procedure J, methyl 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylate was reacted toafford 90 mg 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid which was used in the nextstep without purification. Similar as to described in General Procedure B, 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxylic acid was reacted with ammonium chloride to afford 90 mg of 5-amino-1-(4-iodo-2-pyridyl)pyrazole-3-carboxamide which was used in the next reaction without purification.Similar to as described in General Procedure E, 5-amino-1-(4-iodo-2-pyridyl) pyrazole-3-carboxamide (90 mg) was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one to give 14mg of the title compound (15%). M-i-H = 341.0; 1H NMR (400 MHz, DMSO-d6) oe 8.44 (dd, J= 5.2, 0.8 Hz, 1H), 8.03- 8.00 (m,1H), 7.68 (s, 1H), 7.29, (dd, J= 5.1, 1.5 Hz, 1H), 7.21 (s, 1H), 6.89 (s, 2H), 6.63 (s, 1H), 5.72 (s,1H), 3.41 – 3.34 (m, 2H), 2.81 (s, 3H), 2.48 – 2.43 (m, 1H), 2.26 – 2.17 (m, 1H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H3F3N2

Step A: Preparation of 2-chloro-4-[3-(trifluoromethyl)-lH-pyrazol-l-yl]benzaldehyde A mixture of 2-chloro-4-fluorobenzaldehyde (7.0 g, 44.3 mmol), 3-(trifluoromethyl)- lH-pyrazole (9.03 g, 66.45 mmol) and potassium carbonate (12.2 g, 88.6 mmol) in anhydrous N,N-dimethylformamide (70 mL) was stirred for 2 h at 110 °C. The reaction mixture was cooled to 0 °C, poured into ice water (800 mL) and stirred for 15 min. The precipitate formed was filtered and dried under reduced pressure to afford the title compound (10.2 g), which was used without further purification. H NMR delta 10.4 (s, 1H), 8.00 (m, 2H), 7.85 (d, 1H), 7.77 (m, 1H), 6.70 (d, 1H).

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.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; TAGGI, Andrew, Edmund; MARCUS, Kimberly, Katherine; REDDY, Ravisekhara, P.; WO2014/172191; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 28466-26-4, name is 4-Aminopyrazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

3.0 g of 4-amino-1H-pyrazole (2) was dissolved in a 7.5 g / 160 mL NaHCO3 / tetrahydrofuran mixed solution, 8.6 g of di-tert-butyl dicarbonate was added and reacted at room temperature for 2 days. The solvent was evaporated to dryness on a rotary evaporator, and then dissolved with ethyl acetate, and washed three times with water, aqueous citric acid, and saturated sodium chloride solution; The organic phase was dried over anhydrous magnesium sulfate over night and filtered and evaporated After the crude product was washed with n-hexane, a pure 5.0 g of a pink solid 3 was obtained in a yield of 75%.

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.

Reference:
Patent; Shandong University; Zhang Yingjie; Liang Xuewu; Xu Wenfang; (47 pag.)CN108864057; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5203-77-0, 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. 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

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, 1,3-Dimethyl-1H-pyrazol-5-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of CDI (973 mg, 6.00 mmol) in dry DCM (10.0 mL) under N2 was added Intermediate A1 (1.38 g, 6.00 mmol) as a solid, in four equal portions, over 10 min and the resulting solution maintained at RT for 16 hr. An aliquot of this solution (473 muL, 0.284 mmol) was added to a suspension of Intermediate G2 (100 mg, 0.296 mmol) in anhydrous DCM (5.0 mL) and the reaction mixture kept at RT for 24 hr. The reaction mixture, in its entirety, was purified by flash column chromatography (SiO2, 40 g, MeOH in DCM, 0-10%, gradient elution) to afford the title compound, Example 16, as a yellow solid (108 mg, 59%); Rt 4.60 min (Method 1 basic); m/z 594 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1.27 (9H, s), 2.39 (3H, s), 3.36 (3H, s), 4.06 (2H, s), 5.39 (2H, s), 6.35 (1H, s), 7.22 (1H, d), 7.30 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.60 (1H, dd), 7.64 (1H, d), 8.24 (1H, br s), 8.27 (1H, dd), 8.34 (1H, dd), 8.59 (1H, br s), 8.89 (1H, br s), 8.92 (1H, dd), 10.04 (1H, br s).

The synthetic route of 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; King-Underwood, John; Hardy, George; Murray, Peter John; Williams, Jonathan Gareth; Onions, Stuart Thomas; US2013/29990; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

1.1 Synthesis of Intermediates P Synthesis of 4-(1-(difluoromethyl)-1H-pyrazol-3-yl)-2, 6-difluorobenzaldehyde (P4) In a 150 mL pressure vessel, a suspension of 3-bromo-1H-pyrazole (8 g, 54.43 mmol) cesium carbonate (53.2 g, 163.29 mmol), and difluoroiodomethane (10% wt. in THF, 200 mL, 106.23 mmol) was heated at 45 C. overnight. The reaction mixture was cooled to room temperature and then filtered through Celite. The filter cake was washed with Et2O (3*150 mL). The filtrate was washed with brine, dried over sodium sulfate and carefully concentrated (20 C. bath, 100 mb vacuum) to give ?17 g of a 1.5:1 ratio of regioisomers and solvent still present. This crude material was combined with 3,5-difluoro-4-formylphenylboronic acid (12.65 g, 68.03 mmol), palladium acetate (0.31 g, 1.381 mmol), butyl di-1-adamantylphosphine (1.171 g, 3.265 mmol) and potassium carbonate (22.80 g, 164.96 mmol) in dioxane (150 mL) and water (50 mL) the mixture was degassed for 10 min with argon, then heated at 100 C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduce pressure, the residue was diluted with EtOAc and washed with brine 2x then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (5% to 15% EtOAc/Hex). Mixed fractions were recrystallized (5:1 Hex/EtOAc) and the combined pure product afforded P4. 1H NMR (400 MHz, Chloroform-d) delta 10.35 (d, J=1.0 Hz, 1H), 7.92 (d, J=2.8 Hz, 1H), 7.46 (d, J=9.6 Hz, 2H), 7.24 (t, J=60.5 Hz, 1H), 6.80 (d, J=2.8 Hz, 1H).

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.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Elbert; Kato, Darryl; Link, John O.; Shapiro, Nathan; Yang, Zheng-Yu; (81 pag.)US2020/30327; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics