Tag: M.W:100-200

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

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

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

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

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

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

Application of 2075-46-9, A common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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 4-nitro-1H-pyrazole (2.5 g, 22.11 mmol) in THF (50 mL) wasadded NaH (0.973 g, 24.32 mmol) and the mixture was stirred at rt for 5 mm. To thissuspension was then added CH3I (1.382 mL, 22.11 mmol) and stirred at rt overnight. The reaction mixture was then diluted with EtOAc (2 x 25 mL) and washed with brine (25 mL). The organic layer was concentrated, followed by purification using normal phase chromatography to yield 1-methyl-4-nitro-1H-pyrazole as white solid (1.9 g, 80% yield).?H NMR (400 MHz, CDC13) oe ppm 8.12 (s, 1H), 8.06 (s, 1H), 3.97 (s, 3H).

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

The solution of 4-nitro-1H-pyrazole (SM6, 10 g, 88.44 mmol), NaH(60%, 1.3 eq, 4.60 g, 114.97mmol) and iodomethane (SM7, 25 g, 177 mmol) in Dry DMF (100 ml) was stirred at 0C overnight, and then cooled to room temperature and quenched with water (200 mL) and extracted with EA. The organic layer was dried over anhydrous Na2SO4 to obtain the target compound 12(11 g, 92 % yield).

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

Reference:
Patent; Hangzhou Rex Pharmaceutical Co., Ltd; WANG, Yonghui; ZHOU, Juan; GAO, Yujun; WANG, Dong; HONG, Binbin; SHEN, Ximing; WU, Yaodong; LI, Chunqi; EP3476848; (2019); 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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3469-69-0

1-Trityl-4-iodopyrazole The title compound was prepared by combining 4-iodopyrazole (10 g, 52 mmol), triphenylmethyl chloride (14.4 g, 51.6 mmol), triethylamine (NEt3) (7.2 mL, 52 mmol), and DMF (80 mL). After stirring overnight, the mixture was poured onto ice water. The precipitated solid was collected and recrystallized to give the title compound as a solid, mp 193-194 C. 1H NMR (CDCl3): delta7.11 (m, 6 H), 7.32 (m, 9 H), 7.41 (s, 1 H), 7.67 (s, 1 H).

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; Warner-Lambert Company; US6528510; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1393128-21-6, name is 4-(Methylthio)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H6N2S

To a solution of SB-FF (100 mg, 0.24 mmol) in DMF (2 mL) was added Al (55 mg, 0.48 mmol) and K2CO3 (100 mg, 0.72 mmol) at 19C. The reaction was stirred at 19C for 16 h. The resulting mixture was poured into water (3 ml). The mixture was extracted with EtOAc (2 mL x 3). The combined organic layers was washed with brine (5 mL), dried over Na2S04 and concentrated in vacuum. The residue was purified by silica gel column (Petroleum ether/ethyl acetate = 10/1 to 3/1) to give SB-14 (80 mg, yield: 74%) as a pink solid. 1H NMR: (400 MHz, CDC13) delta 7.53 (s, 1H), 7.43 (s, 1H), 4.79-4.97 (m, 2H), 4.47-4.65 (m, 1H), 2.56-2.63 (m, 1H), 2.35 (s, 3H), 2.19-2.26 (m, 1H), 2.00-2.08 (m, 2H), 1.63-1.92 (m, 5H), 1.35-1.57 (m, 5H), 1.20-1.1.32 (m, 5H), 1.07-1.18 (m, 5H), 0.75-0.91 (m, 1H), 0.71 (s, 3H). LCMS: rt = 1.25 mm, m/z = 449.2 [M+H]+

The synthetic route of 1393128-21-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics