Category: 70951-85-8

70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, 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. name: 4-Bromo-1-(tert-butyl)-1H-pyrazole

General procedure: Pd(dppf)Cl2 (1.45 g, 1.98 mmol) was added to a mixture of 4-bromo-1-(tert-pentyl)-1H-pyrazole (8.6 g, 39.61 mmol), Intermediate 4 (6.56 g, 47.53 mmol), K2CO3 (10.95 g, 79.22 mmol), dioxane (90 mL), and H2O (45 mL) at rt under N2. The mixture was degassed with 3 vacuum/N2 cycles, heated at 80 C. for 4 h, cooled to rt, and then poured into H2O (100 mL). The precipitate was filtered off. The filtrate was diluted with ethyl acetate (200 mL) and H2O (100 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered, concentrated, and then purified by silica gel chromatography (CH2Cl2/CH3OH=100/1?30/1) to give 2.7 g of an impure red solid. HCl in CH3OH (4M, 30 mL) was added. The solution was stirred at rt for 2 h, concentrated, diluted with ethyl acetate (15 mL), and then stirred overnight. The solids were filtered, washed with ethyl acetate (10 mL), and dried to give 4-(1-(tert-pentyl)-1H-pyrazol-4-yl) pyridin-2-amine hydrochloride (3.1 g). This material was dissolved in H2O (5 mL). Aqueous potassium carbonate (2 M, 8 mL) was added slowly until pH=9-10. The mixture was extracted with ethyl acetate (20 mL×6). The combined organics were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated to give 4-(1-(tert-pentyl)-1H-pyrazol-4-yl) pyridin-2-amine (2.35 g, 90%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 8.24 (s, 1H), 7.84-7.83 (m, 2H), 6.75-6.73 (m, 1H), 6.60 (s, 1H), 5.74 (s, 2H), 1.87-1.81 (m, 2H), 1.52 (s, 6H), 0.62 (t, 3H); LCMS: 231.2 [M+H]+.

The synthetic route of 70951-85-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Metacrine, Inc.; SMITH, Nicholas D.; GOVEK, Steven P.; DOUGLAS, Karensa L.; LAI, Andiliy G.; US2020/102308; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 70951-85-8, The chemical industry reduces the impact on the environment during synthesis 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of 4-bromo-1-(1 ,1-dimethylethyl)-1 H-pyrazole (2.4g, 1 1.82mmol), 4.4.4′.4′.5.5.5′.5′-octamethyl-2,2′-bi-1 ,3,2-dioxaborolane (3.00g, 1 1.82mmol), potassium acetate (2.90g, 29.5mmol), tris(dibenzylideneacetone)dipalladium (0) (0.108g, 0.1 18mmol), 2-(dicyclohexylphosphino)-2′.4′,6′-triisopropylbiphenyl (0.225g, 0.473mmol) in 1 ,4-dioxane (30ml) was degassed with nitrogen. The reaction mixture was spilt into 2 microwave vials and heated at 1 10C in a microwave for 1 .5h. There was no starting material remaining so the reactions were filtered through a bond elut reservoir and the residue was washed with ethyl acetate. The filtrate was concentrated in vacuo to yield the crude product. This was dissolved in DCM and purified through silica (50g) eluting with 0-50% ethyl acetate in DCM gradient. Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a beige solid (1.68g).LCMS (Method B): Rt = 1 .08min, MH+ = 250.8

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-1-(tert-butyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander George Steven; WILSON, David Matthew; WO2011/134971; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, 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 70951-85-8, HPLC of Formula: C7H11BrN2

Stage d) Preparation of 1-(1,1-Dimethylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 11) To a 20 L four-neck bottle, 4-bromo-(tert-butyl)pyrazole (1.15 kg, 5.66 mol) and THF (9.2 L) were added, then the mixture was cooled to between -78 C. and -85 C. and treated with nBuLi (6.23 mol) dropwise at that temperature. After addition the solution was stirred at the same temperature for 1 h and isopropyl pinacol borate (1.47 kg, 7.92 mol) was added dropwise. The reaction was complete after stirring for ?3 h (starting material<1.0% a/a by GC) then water (2.3 L) was added to quench the reaction; and the pH adjusted to 8-9 by addition of 3.45 kg 1M HCl. The aqueous phase was extracted with TBME (3.45 L*2), and the combined organic phase washed with 5% NaCl (3.45 L*2) and water (3.45 L) in sequence. The organic phase was evaporated to give the crude product. After subsequent recrystallization from heptanes the pure product was obtained as a white solid (GC purity 99.7% a/a) in a 63.5% th overall yield. (Two 20 L reactions were run, then combined in the heptane recrystallization). 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. Reference:
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, molecular formula is C7H11BrN2, 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. Product Details of 70951-85-8

A mixture of 4-bromo-1-tert-butyl-1H-pyrazole (3.3 g, 16.3 mmol), bis(pinacolato)diboron (8.3 g, 32.6 mmol), PdCl2(dppf) (1.8 g, 2.4 mmol), and KOAc (3.2 g, 32.6 mmol) in 1,4-dioxane (60 mL) was heated at reflux for 15 hours. After the completion of the reaction, the mixture was filtered and the filter cake was washed with EtOAc (100 mL). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography using heptane/ethyl acetate (10% to 50%) as eluting solvents to afford 1-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as white solid (1.0 g, 25%). MS (ESI) m/z: 251 [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 70951-85-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); 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. 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Isopropyl magnesium chloride lithium chloride complex (1.3 M in THF, 28.4 mL, 37 mmol) was charged to a solution of 4-bromo-1-(tert-butyl)-1H-pyrazole (5.0 g, 25 mmol) in anhydrous THF (25 mL) under argon at ambient temperature. Anhydrous dioxane (3.3 g, 37 mmol) was charged to the reaction, and the reaction was agitated at 45 00 for 4 h. The resulting mixture was cooled to ambient temperature and charged to an anhydrous solution of acetic anhydride (7.5 g, 73 mmol) in THF (25 mL) at -20 00 The resulting mixture was warmed to ambient temperature and concentrated to a residue. The mixture was dissolved in methyl t-butyl ether (50 mL) and washed with water (25 mL). The organic portion was concentrated to provide crude 1-(1-(tert-butyl)-1H-pyrazol-4-yl)ethan-1-one as an oil (7.6 g, 36 wt%) and 67% yield. Crystallization in a mixture of methyl t-butyl ether and heptane provided analytically pure material 1 -(1 -(tert-Butyl)-1 H-pyrazol-4-yl)ethan-1 -one. NMR (500 MHz, ODd3) = 7.96 (s, 1 H), 7.86 (s, 1 H), 2.37 (s, 3H), 1.55 (s, 9H).

According to the analysis of related databases, 70951-85-8, the application of this compound in the production field has become more and more popular.

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. 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-(tert-butyl)-1H-pyrazole

A solution of 4-bromo-1-tert-butyl-1H-pyrazole (973 mg, 4.79 mmol) in anhydrous THF (9.5 ml) was cooled to -78 C. under argon. A solution of n-BuLi in Hexanes (1.6 M, 3.2 mL, 5.12 mmol) was then added dropwise over 5 min and reaction mixture was stirred at -78 C. for 80 min. A solution of N-methoxy-N-methylacetamide (0.55 ml, 5.17 mmol) in THF (3 mL) was added dropwise and mixture was warmed to 0 C. After 4 hours, reaction mixture was quenched via addition of NH4Cl (aq) (10 mL) and mixture was extracted with ethyl acetate. Combined organic layers were washed with 50% brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to yield 1-(1-tert-butyl-1H-pyrazol-4-yl)ethanone 5.14.

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.

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. 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-(tert-butyl)-1H-pyrazole

A solution of 4-bromo-1-tert-butyl-1H-pyrazole (973 mg, 4.79 mmol) in anhydrous THF (9.5 ml) was cooled to -78 C. under argon. A solution of n-BuLi in Hexanes (1.6 M, 3.2 mL, 5.12 mmol) was then added dropwise over 5 min and reaction mixture was stirred at -78 C. for 80 min. A solution of N-methoxy-N-methylacetamide (0.55 ml, 5.17 mmol) in THF (3 mL) was added dropwise and mixture was warmed to 0 C. After 4 hours, reaction mixture was quenched via addition of NH4Cl (aq) (10 mL) and mixture was extracted with ethyl acetate. Combined organic layers were washed with 50% brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to yield 1-(1-tert-butyl-1H-pyrazol-4-yl)ethanone 5.14.

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.

Application of 70951-85-8, 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. 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a -78 0C solution of 4-bromo-l -7-butyI-lH-pyrazole (15 g, 74.3 mmol) in anhydrous THF (100 mL) was added /7-BuLi (2.5 M in hexane, 53 mL, 132 mmol) under N2, and the resulting mixture was stirred at -78C for 30 min. Excess dry ice was added at -78 0C, and the mixture was warmed slowly to RT and stirred overnight. The reaction was concentrated in vacuo, water was added and the pH was adjusted to pH 3 by the addition of 2N aq HCI. The aqueous solution was extracted with EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was recrystallized (EtO Ac-pet, ether) to give 1 -/-butyl- lH-pyrazole-4-carboxylic acid (8.0 g, 67 % yield). 1H NMR (300 MHz, CDCl3): ^ 8.10 (s, 1 H), 8.03 (s, 1 H), 1.64 (s, 9 H); MS (ESI) m/z: 168.9 [M+Hf.

The synthetic route of 4-Bromo-1-(tert-butyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

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. 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a -78 0C solution of 4-bromo-l -7-butyI-lH-pyrazole (15 g, 74.3 mmol) in anhydrous THF (100 mL) was added /7-BuLi (2.5 M in hexane, 53 mL, 132 mmol) under N2, and the resulting mixture was stirred at -78¡ãC for 30 min. Excess dry ice was added at -78 0C, and the mixture was warmed slowly to RT and stirred overnight. The reaction was concentrated in vacuo, water was added and the pH was adjusted to pH 3 by the addition of 2N aq HCI. The aqueous solution was extracted with EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was recrystallized (EtO Ac-pet, ether) to give 1 -/-butyl- lH-pyrazole-4-carboxylic acid (8.0 g, 67 percent yield). 1H NMR (300 MHz, CDCl3): ^ 8.10 (s, 1 H), 8.03 (s, 1 H), 1.64 (s, 9 H); MS (ESI) m/z: 168.9 [M+Hf.

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 70951-85-8.

Reference of 70951-85-8,Some common heterocyclic compound, 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, molecular formula is C7H11BrN2, 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 an oven dried, N2-flushed, small round bottom flask was added 4-bromo-1-(tert-butyl)-1H-pyrazole (0.396 g, 1.95 mmol). The flask was sealed and purged with nitrogen. 5 mL anhydrous THF was added and the reaction was cooled to -78 C. n-Butyl lithium (0.93 mL, 2.24 mmol) was added and the reaction was stirred at -78 C. for 30 minutes. 2-(4-cyclohexyl-3,4-dimethyl-2,5-dioxoimidazolidin-1-yl)acetaldehyde (112b) (0.446 g, 1.77 mmol) in 3 mL was then added to the flask at -78 C. The reaction was stirred for 2 hours at -78 C. and quenched with water. The mixture was extracted with ethyl acetate (3¡Á10 mL). The combined organics were dried with Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography utilizing a Silicycle column (12 g) and elution with 20-100% ethyl acetate/hexane to afford 200 mg (50%) of product as an off white solid.

The synthetic route of 70951-85-8 has been constantly updated, and we look forward to future research findings.