Month: August 2021

Reference of 89717-64-6, 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. 89717-64-6 name is 4-Bromo-3-nitro-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.

Example 7(5S)-5-Amino-7-hvdroxy-2-[3-(trifluoromethyl)phenyll-2,4,5J-tetrahydro-6/-/-pyrazolo[3,4- iblPyridin-6-one, HCI salt (7) 7Step 1 . Synthesis of 4-bromo-3-nitro-1-[3-(trifluoromethyl)phenyll-1 /-/-pyrazole (C56). Pyridine (99%, 0.512 mL, 6.27 mmol) and [3-(trifluoromethyl)phenyl]boronic acid (649 mg, 3.42 mmol) were added to a solution of 4-bromo-3-nitro-1 /-/-pyrazole (596.6 mg, 3.108 mmol) in tetrahydrofuran (9 mL); copper(ll) acetate (99%, 855 mg, 4.66 mmol) was then added, and the reaction was stirred for 42 hours. The reaction mixture was filtered through Celite and concentrated in vacuo, then partitioned between EtOAc (5 mL) and water (5 mL). The aqueous layer was extracted with EtOAc (3 x 5 mL), and the combined organic layers were washed with water (5 mL) and dried over sodium sulfate. After filtration and removal of solvent under reduced pressure, the residue was purified via silica gel chromatography (Gradient: 0% to 20% EtOAc in heptane) to provide C56. The regiochemistry of C56 was assigned based on NOE experiments. Yield: 779 mg, 2.32 mmol, 75%. GCMS m/z 335, 337 (M+). H NMR (400 MHz, CDCI3) delta 7.68-7.76 (m, 2H), 7.94-7.98 (m, 1 H), 7.99-8.01 (m, 1 H), 8.14 (s, 1 H

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

Reference:
Patent; PFIZER INC.; DOUNAY, Amy Beth; MCALLISTER, Laura Ann; PARIKH, Vinod D; RONG, Suobao; VERHOEST, Patrick Robert; WO2012/73143; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2817-71-2, name is 1-Ethylpyrazole, molecular formula is C5H8N2, 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: 1-Ethylpyrazole

General procedure: In athree-necked bottle, 0.82 g (10 mmol)1-methylpyrazole and 1.25 g(10mmol) bromoethanolwere added into 10mL CH3CN. Then, themixtureswere stirred at reflux temperature for 48 h in a nitrogen atmosphere.After the reaction, the volatiles were removed under reducedpressure. The residual was washed several times by ethyl acetate togive a white solid. After filtration and drying in vacuum, the pureHEMPzBr was obtained: 1.532 g, yield 74%, white solid. 1H NMR(400 MHz, DMSO-d6) delta 8.58 (dd, J = 21.9, 2.8 Hz, 2H, Pz-H), 6.86 (t, J = 3.1 Hz, 1H, Pz-H), 5.26 (s, 1H, -OH), 4.61 (t, J = 5.0 Hz, 2H, -CH2-),4.20 (s, 3H, -CH3), 3.76 (t, J = 5.2 Hz, 2H, -CH2-).13C NMR (101 MHz,D2O) delta 138.38, 137.98, 107.43, 59.34, 52.34, 37.61. HR-MS (QTOF)calcd. for [C6H11N2O+] (m/z): 127.0866, found: 127.0868.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2817-71-2, its application will become more common.

Reference:
Article; Wang, Tengfei; Ma, Yuan; Jiang, Jiamin; Zhu, Xinrui; Fan, Baowan; Yu, Guanyao; Li, Ningning; Wang, Shasha; Ren, Tiegang; Wang, Li; Zhang, Jinglai; Journal of Molecular Liquids; vol. 293; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, 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 138786-86-4, Safety of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 27 Methyl 4-nitro-1-trityl-1H-pyrazole-3-carboxylate To a solution of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (5.0 g, 29.0 mmol) and triethylamine (4.5 mL, 32.0 mmol) in DMF (50 mL), trityl chloride (8.9 g, 32.0 mmol) was added at 0 C., and the mixture was stirred at room temperature for 4 hr. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1) to give the title compound (7.3 g, yield 61%). 1H-NMR (CDCl3): delta 3.28 (3H, s), 7.14-7.19 (5H, m), 7.30-7.35 (10H, m), 8.11 (1H, s).

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, Methyl 4-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-13-1, name is 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. Quality Control of 1H-Pyrazole

4-Nitropyrazole is available commercially from the N.D. Zelinsky Institute, Organic Chemistry, Leninsky prospect 47, 117913 Moscow B-334, Russia. The compound may also be prepared as follows :-; Fuming nitric acid (9.5 ml) was added drop wise to a stirred solution of pyrazole (13.6 g) in glacial acetic acid (51 ml) that had been cooled to -10°C using an ice-salt bath. A voluminous precipitate was formed. Acetic anhydride (27 ml) was added dropwise and the resultant mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured onto ice and the acidity of the mixture was reduced to peta5 by the addition of potassium carbonate. The precipitate was isolated by filtration. The resultant solid was dissolved in water and the aqueous solution was extracted with diethyl ether. The organic solution was dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-800C, 50 ml) 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. This solid was believed to be 1-nitropyi-azole (20.6 g); 1H NMR Spectrum: (DMSOd6) 6.71 (s, IH), 7.88 (s, IH), 8.81 (s, IH). The compound may be explosive and should be handled cautiously.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 612511-81-6, 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 612511-81-6 as follows.

A mixture of (1 -methyl-1 H-pyrazol-3-yl)methanamine (383 mg, 3.45 mmol) and 2-bromo-1 – methoxy-3-nitrobenzene (400mg, 1 .724 mmol) in 1 ,4-dioxane (3.5 mL) was stirred into a sealed vessel at 120 °C overnight. The reaction was then heated at 150 “C for 24 hours followed by 120 over the weekend. The reaction was concentrated in vacuo, and the resulting residue was purified by silica gel chromatography (0-50percent EtOAc/hexanes) to afford the desired product (288 mg) as an orange oil. LC-MS (ES) m/z = 263 [M+H]+.

According to the analysis of related databases, 612511-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 36650-74-5, The chemical industry reduces the impact on the environment during synthesis 36650-74-5, name is 1H-Pyrazole-3-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of II-D12 (165 mg, 0.4 mmol) in acetone (5 mL) was added K2C03 (96.9 mg, 0.7 mmol) and lH-pyrazole-4-carbonitrile (65.4 mg, 0.7 mmol) at l5C. The reaction mixture was stirred for 16 hours at l5C. The reaction mixture was added into saturated NH4Cl (20 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with saturated brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated to give product. The residue was purified by combi flash (0-20% of EtOAc in PE) to give II-D13 (74.6 mg, 44.1%) as a solid. (1069) 1H NMR (400 MHz, CDCl3) dH 7.47 (d, J= 2.4 Hz, 1H), 6.72 (d, J= 2.4 Hz, 1H), 4.96 (dd, J = 17.6, 51.2 Hz, 2H), 3.52 (q, J = 6.8 Hz, 2H), 3.21 (s, 2H), 2.59 (t, J = 8.8, 1H), 2.25-2.10 (m, 2H), 1.90-1.60 (m, 6H), 1.55-1.10 (m, 18H), 1.05-0.80 (m, 5H), 0.68 (s, 3H); MS ESI calcd. for C29H42N302 [M-H20+H]+ 464, found 464.

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, 1H-Pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (276 pag.)WO2019/126741; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, 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 3398-16-1, Product Details of 3398-16-1

General procedure: 4.4.1. Ethyl 5-amino-2-phenylpyrazolo[1,5-a]quinoline-3-carboxylate (13aa). A mixture of 2-fluorobenzonitrile 6a (121 mg,1.00 mmol), 12a (280 mg, 1.20 mmol) and Cs2CO3 (980 mg,3.00 mmol) in DMSO (5.0 mL) was stirred at 120 C for 16 h. Aftermonitoring the end of the reaction on TLC, the mixture was cooledto room temperature and diluted with water. The resulting mixturewas extracted with ethyl acetate twice. The combined organiclayers were washed with water twice, dried over MgSO4 and thesolvent was removed in vacuo to afford a residue. The residue waspurified by flash column chromatography (hexane:EtOAc1:1) onsilica gel to afford pyrazolo[1,5-a]quinoline 13aa (137 mg, 41percentyield).

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, 4-Bromo-3,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kato, Jun-Ya; Ijuin, Ryosuke; Aoyama, Hiroshi; Yokomatsu, Tsutomu; Tetrahedron; vol. 70; 17; (2014); p. 2766 – 2775;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5775-86-0, name is 4-Bromo-1,5-dimethylpyrazole, 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 5775-86-0, Safety of 4-Bromo-1,5-dimethylpyrazole

To a solution of 1.5 (lg, 3.22mmol, leq) in 1,4- dioxane (7 .2mL) and water (2. 8mL) was added 4-bromo- 1,5 -dimethyl- 1 H-pyrazole (0. 780g, 4.83mmol,1.5eq),and potassium carbonate (1.27g, 9.67mmol, 3eq).The reaction mixture was degassed by argon for 30 mm. [1,1 ?-Bi sdiphenylphosphinoferrocene]palladium(II) dichloride CH2C12 complex (0.080g, 9.67mmol, 0.O3eq), was added into reaction mixture and again reaction mixture was degassed by argon for 30 mm. Further reaction mixture was stirred at 100C for 4h. Upon completion, reaction mixture transferred into water and extracted with ethyl acetate. Organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 20% ethyl acetate in hexane to obtain pure 631.6 (0.530g, 59.06%). MS(ES): m/z 279.37 [M+H]t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1,5-dimethylpyrazole, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 42098-25-9, The chemical industry reduces the impact on the environment during synthesis 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Intermediate 2 5-(3A-Dihydro-2H-pyran-6-yl)-1-methyl-4-nitro-1H-pyrazole A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole (200 mg, 1.25 mmol), potassium fluoride dihydrate (235 mg, 2.5 mmol) and 3,4-dihydro-2H-pyran-6-boronic acid pinacol ester (394 mg, 1.88 mmol) in THF (3 mL) was degassed by bubbling nitrogen through it for 15 min. Tris(dibenzylideneacetone)dipalladium/tri-tert-butyl phosphonium tetrafluoroborate mixture (mole ratio: 1/1.2, 151 mg, 0.13 mmol) was added and the mixture degassed for a further 10 min before being heated in the microwave at 85 C. for 2 hr. Water (10 mL) was added and the mixture extracted with EtOAc (3*5 mL). The combined organic layers were passed through a phase separation cartridge and concentrated under reduced pressure. Purification via silica gel chromatography (0-5% EtOAc/isohexane) gave 5-(3,4-dihydro-2H-pyran-6-yl)-1-methyl-4-nitro-1H-pyrazole as a yellow solid (215 mg, 82%). 1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 5.22 (t, J=3.9 Hz, 1H), 4.20 (t, J=5.1 Hz, 2H), 3.88 (s, 3H), 2.31-2.24 (m, 2H), 2.05-1.96 (m, 2H).

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-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Burch, Jason; Sun, Minghua; Wang, Xiaojing; Blackaby, Wesley; Hodges, Alastair James; Sharpe, Andrew; US2014/88117; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 5-amino-3-methylpyrazole (1 mmol), isatin or acenaphthylene-1,2-dione (1 mmol), thioacid (1 mmol), and p-TSA (30 mol %) in CH3CN (5 mL) was stirred at 80 C for 12-24 h. After completion of the reaction confirmed by TLC (eluent acetone/petroleum ether, 1:2), the reaction mixture was cooled to room temperature. Then, the solvent was removed under vacuum. The solid was recrystallizated from CH3CN and ethanol to afford the pure 4 or 6 as a white or yellow powder.

The chemical industry reduces the impact on the environment during synthesis 5-Amino-1,3-dimethylpyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Hui; Shi, Daqing; Tetrahedron; vol. 67; 31; (2011); p. 5686 – 5692;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics