Category: 5744-80-9

Related Products of 5744-80-9, A common heterocyclic compound, 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, molecular formula is C5H7BrN2, 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.

Example 173 3-amino-5-(dicyclopropylmethyl)-7-(1,5-dimethyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (0879) A mixture of 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (300 mg) obtained in Example 78, Step C, 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (283 mg), tetrakis(triphenylphosphine)palladium(0) (107 mg), potassium acetate (182 mg) and N,N-dimethylacetamide (4 mL) was stirred under an argon atmosphere at 110C for 4 hr. The reaction mixture was cooled to room temperature, 3-bromo-1,5-dimethyl-1H-pyrazole (195 mg), aqueous sodium carbonate solution (2 M, 0.928 mL) and tetrakis(triphenylphosphine)palladium(0) (107 mg) were added. Under an argon atmosphere, the reaction mixture was stirred at 130C for 5 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate) and further purified by silica gel chromatography (diol silica gel, hexane/ethyl acetate). The obtained solid was crystallized from ethyl acetate/diisopropyl ether to give the title compound (104 mg).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H7BrN2

The title compound was obtained in analogy to example 48, intermediate a, from tert-butyl 4- oxo- 1 -phenyl- 1,3 ,8-triazaspiro [4. 5]decane-8-carboxylate (example 35, intermediate c) and 3- bromo-1,5-dimethyl-1H-pyrazole (CAS RN 5744-80-9) at 120C over 19 hours as a colorlesssolid. MS (ESI): mlz = 426.25 [M+H]; To a suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3, 8-triazaspiro [4.51 decane- 8-carboxylate (100 mg, 302 imol, example 35, intermediate c) and 1-ethyl-3-iodo-1H-pyrazole (67 mg, 302 imol, CAS RN 120278 1-34-7) in dioxane (2 mL) were added K2C03 (125 mg, 905 imol), DMEDA(6.11 iL, 48.3 imol, CAS RN 110-70-3) and Cul (4.6 mg, 24.1 imol) and the mixture was purged with argon. The suspension was heated to 100C and stuffed at this temperature over 14 hours. The reaction mixture was filtered over a microfilter, the filtrate was washed with a small volume of EtOAc and MeOH, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system elutingwith a gradient of n-heptane : EtOAc (100: 0 to 50: 50) to give the title compound as a colorless solid (0.107 g; 83.3%).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; RUDOLPH, Markus; SATZ, Alexander Lee; (204 pag.)WO2017/5583; (2017); 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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C5H7BrN2

General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+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:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1562 – 1576;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5744-80-9, A common heterocyclic compound, 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, molecular formula is C5H7BrN2, 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.

Example 173 3-amino-5-(dicyclopropylmethyl)-7-(1,5-dimethyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (0879) A mixture of 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (300 mg) obtained in Example 78, Step C, 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (283 mg), tetrakis(triphenylphosphine)palladium(0) (107 mg), potassium acetate (182 mg) and N,N-dimethylacetamide (4 mL) was stirred under an argon atmosphere at 110C for 4 hr. The reaction mixture was cooled to room temperature, 3-bromo-1,5-dimethyl-1H-pyrazole (195 mg), aqueous sodium carbonate solution (2 M, 0.928 mL) and tetrakis(triphenylphosphine)palladium(0) (107 mg) were added. Under an argon atmosphere, the reaction mixture was stirred at 130C for 5 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate) and further purified by silica gel chromatography (diol silica gel, hexane/ethyl acetate). The obtained solid was crystallized from ethyl acetate/diisopropyl ether to give the title compound (104 mg).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Bromo-1,5-dimethyl-1H-pyrazole

The title compound was obtained in analogy to example 48, intermediate a, from tert-butyl 4- oxo- 1 -phenyl- 1,3 ,8-triazaspiro [4. 5]decane-8-carboxylate (example 35, intermediate c) and 3- bromo-1,5-dimethyl-1H-pyrazole (CAS RN 5744-80-9) at 120C over 19 hours as a colorlesssolid. MS (ESI): mlz = 426.25 [M+H]; To a suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3, 8-triazaspiro [4.51 decane- 8-carboxylate (100 mg, 302 imol, example 35, intermediate c) and 1-ethyl-3-iodo-1H-pyrazole (67 mg, 302 imol, CAS RN 120278 1-34-7) in dioxane (2 mL) were added K2C03 (125 mg, 905 imol), DMEDA(6.11 iL, 48.3 imol, CAS RN 110-70-3) and Cul (4.6 mg, 24.1 imol) and the mixture was purged with argon. The suspension was heated to 100C and stuffed at this temperature over 14 hours. The reaction mixture was filtered over a microfilter, the filtrate was washed with a small volume of EtOAc and MeOH, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system elutingwith a gradient of n-heptane : EtOAc (100: 0 to 50: 50) to give the title compound as a colorless solid (0.107 g; 83.3%).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; RUDOLPH, Markus; SATZ, Alexander Lee; (204 pag.)WO2017/5583; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5744-80-9, 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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.

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

Synthetic Route of 5744-80-9, A common heterocyclic compound, 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, molecular formula is C5H7BrN2, 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.

General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+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.