Category: 13808-64-5

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

To a solution of 4-bromo-3-methyl-1H-pyrazole 1a (500 mg, 3.1 mmol) in 8 mL DMF was added NaH (60%purity, 149 mg, 6.2 mmol), ethyl 2-bromoacetate (570 mg, 3.4 mmol) and KI (489 mg, 2.9 mmol). The mixture was stirredat 80C for 12 h. To the reaction mixture was added H2O (20 mL), extracted with EA (20 mL*3), combined the organicphase, washed with H2O (20 mL*2), saturation NaCl solution (20 mL*2), dried over Na2SO4, filtered, the filtrate wasconcentrated under reduced pressure. The residue was purified by silica column chromatography (Eluent C) to give titleproduct ethyl 2-(4-bromo-3-methyl-1H-pyrazol-1-yl)acetate 1b (522 mg, pale yellow liquid), yield: 68.0%1H NMR (400 MHz, CDCl3) delta 7.44 (d, 1 H), 4.85 (s, 1H), 4.79 (s, 1H), 4.24 (q, 2 H), 2.23 (s, 3H), 1.29 (t, 3 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; Medshine Discovery Inc.; Quingdao Huanghai Pharmaceutical Co., Ltd.; WU, Chengde; ZHANG, Zhiliu; YU, Tao; (125 pag.)EP3042907; (2016); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).4-bromo-1 ,5-dimethyl-1H-pyrazole10331] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.41 (s, 1H),3.76 (s, 3H), 2.22 (s, 3H)4-bromo-1 ,3-dimethyl-1H-pyrazole10332] ?H NMR (500 MHz, dmso-d6) oe ppm: 7.81 (s, 1H),3.74 (s, 3H), 2.09 (s, 3H)

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; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5BrN2

A mixture of (bromomethyl) benzene (1.3 g, 7.6 mmol) , 4-bromo-3-methyl-1H-pyrazole (1.01 g, 6.27 mmol) and potassium carbonate (2.1 g, 15 mmol) in DMF (15 mL) was stirred at 50 for 6 h. The reaction mixture was diluted with water (30 mL) . The resulting mixture was extracted with EtOAc (30 mL × 3) . The combined organic layers were washed with saturated aqueous NaCl (20 mL) , dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 5/1 to give a light yellow mixture of isomerides (806 mg, 51.2) .[1663]MS (ESI, pos. ion) m/z: 251.10 [M+1]+.

According to the analysis of related databases, 13808-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 13808-64-5

4-Bromo-1-isopropyl-3-methyl-1H-pyrazole (B2.1) (0353) A mixture of 4-bromo-3-methyl-1H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), Cs2CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C. for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (UV214, PE_DMC=100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H]+=203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 13808-64-5, These common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, 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.

A solution of 4-bromo-3-methyl-1H-pyrazole 1a (500 mg, 3.13 mmol), Cs2CO3 (2.04 g, 6.25 mmol) and 1-chloropropan-2-one (862 mg, 9.38 mmol) in DMF (3 mL) was stirred at 90 C under MW for 1.5 h. The reaction mixturewas cooled to room temperature and water (15 mL) was added. It was extracted with DCM (30 mL*3), and the organiclayers were combined and washed with water (15 mL*2) and brine (15 mL * 2), dried over Na2SO4, filtrated and evaporated.The residue was purified by column to give 1-(4-bromo-3-methyl-1H-pyrazol-1-yl)propan-2-one 1b (700 mg, crude) asa yellow oil.1H NMR (400 MHz, CDCl3) delta 7.50 (d, 1H), 4.86 (d, 2H), 2.31-2.15 (m, 6H)

Statistics shows that 4-Bromo-3-methylpyrazole is playing an increasingly important role. we look forward to future research findings about 13808-64-5.

Application of 13808-64-5, A common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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 suspension of NaH (60%, 2.5 g, 62.9 mmol) in THF (800 mL), was dropwise added 4-bromo-3-methyl-lH-pyrazole (10 g, 62.9 mmol) in 100 ml THF at 0 C. After stirred at the same temperature for 30 min, BnBr (4.4 ml, 62.9 mmol) was added at 0 C. The reaction mixture was stirred at 15 C for 1 h and carefully quenched with ice-water. The resulting mixture was extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine (2x 100 mL), dried over anhydrous Na2S04 and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc =4/1 to 1/1) to give the title compound (6 g, yield : 60%); m/z (ES+) : 251 [M+H]+.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 13808-64-5,Some common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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-bromo-3 -methyl- lH-pyrazole 1 (161 mg, 1 mmol) in pyridine (1 mL) was added 2,5-difluorophenyl boronic acid (240 mg, 1.5 mmol), and 4A molecular sieves. The mixture was stirred for 72 h at room temperature. The reaction was worked-up with saturated NaHC03and EtOAc extraction. The organic layer was separated and aqueous was extracted with EtOAc. The combined organic phase was dried over a2S04, filtered, and concentrated to give crude product. The crude product was purified on ISCO columns. Fractions containing pure product were combined and evaporated to give 43 (100 mg, 37%) as a blue wax.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 13808-64-5, The chemical industry reduces the impact on the environment during synthesis 13808-64-5, name is 4-Bromo-3-methylpyrazole, I believe this compound will play a more active role in future production and life.

(1) Combine 16.1 g (0.1 mol) of 4-bromo-3-methyl-1H-pyrazole, 10.1 g (0.12 mol) of 3,4-dihydro-2H-pyran, and 0.7 g (0.006 mol) of trifluoroacetic acid ) Add to the reaction bottle and stir to heat to micro-reflux for 12 hours. The reaction formula is as follows:Cool to room temperature, add 0.24 g (0.006 mol) of sodium hydride to neutralize the reaction system,Vacuum distillation to obtain intermediate4-bromo-3-methyl-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole and4-bromo-5-methyl-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole total 24 grams,The presence of isomers does not affect the next reaction. (2) The intermediates obtained in step (1) 4-bromo-3-methyl-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole and 4-bromo-5- Methyl-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole 24 g was dissolved in 200 ml of THF, cooled to minus 75 degrees, and n-butyl with a concentration of 2.5 mol / L was added dropwise 48 ml (0.12 mol) of lithium solution, maintaining the temperature at minus 75 degrees Celsius, dropping and holding for half an hour, then adding 14 g (0.12 mol) of N-formylmorpholine at this temperature, the reaction formula in step (2) is as follows :After the reaction is completed, naturally warm to room temperature, add dilute sulfuric acid to quench until the system pH value is less than 1, stir at room temperature for 3-4 hours, neutralize with sodium bicarbonate, extract with ethyl acetate, dry and concentrate to obtain the target product by adsorption and purification on silica gel 3-Methyl-1H-pyrazole-4-carbaldehyde 8 g.The yield of the target product 3-methyl-1H-pyrazole-4-carbaldehyde in this example was 72.7%. 2 is the nuclear magnetic resonance spectrum of the product 3-methyl-1H-pyrazole-4-carbaldehyde obtained in this example;

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-methylpyrazole, other downstream synthetic routes, hurry up and to see.

Electric Literature of 13808-64-5, These common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, 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 4554-{7-Methanesulfonyl-5- [(S)-oxan-4-yl(phenyl)methylj -5H-pyrido [3,2-bj indol-3-yl}-3-methyl- 1H-pyrazole (S)-(7-(Methylsulfonyl)-5 -(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrido [3 ,2-b]indol-3 -yl)boronic acid (20.0 mg, 0.0430 mmol) and 4-bromo-3 -methyl-i Hpyrazole (13.9 mg, 0.0860 mmol) were dissolved in in 1.5 mL of dioxane and and 0.2 mLof water. To this was added potassium carbonate (17.9 mg, 0.129 mmol) and PdC12(dppf)-CH2C12 adduct (2.46 mg, 3.02 .imol), and argon was bubbled in while sonicating for 5 mm. The vial was capped, heated at 100 C for 50 mm, and filtered. The crude material was purified via preparative LC/MS (Preparative HPLC Method 1) with the following modifications: Gradient 10-50% B over 40 mm. Fractions containing thedesired product were combined and dried via centrifugal evaporation. The yield of the product was 1.20 mg, and its estimated purity by LCMS analysis was 96%. Two analytical LC/MS injections were used to determine the final purity Injection 1: LC/MS Method 3, HPLC RT = 1.83 mm. Injection 2: LC/MS Method 4, HPLC RT = 2.37 mm. ?H NMR (500MHz, DMSO-d6) oe 8.69 (s, 2H), 8.42 (d, J=8.4 Hz, 1H), 8.27 (br. s., 1H),8.01 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.36 (t, J=7.5 Hz, 2H), 7.27 (t, J=7.3 Hz, 1H), 5.99 (d, J=i 1.0 Hz, 1H), 3.90 (s, 2H), 3.72 (d, J=9.9 Hz, 2H), 3.60 (br. s., 2H), 3.52 (t,J=ii.2 Hz, 3H), 3.27 (t,J=ii.6 Hz, 1H), 2.43 (s, 3H), 1.85-1.73 (m, 1H), 1.72-1.58 (m, 1H), 1.46-1.27 (m, 1H), 0.89 (d,J=12.i Hz, 1H).

The synthetic route of 13808-64-5 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H5BrN2

Example 12 Synthesis of 2-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-2-methylcyclopentanone (194) 2-(4-bromo-3-methylpyrazol-1-yl)cyclopentanone and 2-(4-bromo-5-methylpyrazol-1-yl)cyclopentanone: To a solution of 4-bromo-3-methyl-1H-pyrazole (10 g, 62.11 mmol) in DMF (60 mL) was added NaH (3.23 g, 80.75 mmol, 60% purity) at 0 C. and stirred at 15 C. for 1 h. Then 2-chlorocyclopentanone (8.84 g, 74.53 mmol, 7.43 mL) was added to the mixture and stirred at 15 C. for 15 h. The reaction mixture was quenched by addition aq. NH4Cl (300 mL) at 0 C., and then extracted with EtOAc (3*100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:MTBE=2:1 to 1:1) to give the mixture of 2-(4-bromo-3-methylpyrazol-1-yl)cyclopentanone and 2-(4-bromo-5-methylpyrazol-1-yl)cyclopentanone as a yellow gum. LCMS: RT 2.119 min, m/z=243.1 [M+H]+.

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 13808-64-5.