Category: 73387-52-7

Some common heterocyclic compound, 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, molecular formula is C10H9BrN2, 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: 5-(4-Bromophenyl)-1-methyl-1H-pyrazole

Inside an argon filled glove bag, 3.41 g of sodium f-butoxide was placed in an oven-dried flask. 7.03 g of 5-(4-bromophenyl)-1 -methyl-1 /-/-pyrazole, 0.328 g of palladium acetate, and 0.7720 g of 1 ,1 ‘-bis(di-i-propylphosphino)-ferrocene were added, and the mixture was evacuated/nitrogen filled three times. 50 ml_ of anhydrous 1 ,4-dioxane was added, followed by the addition of 7.00 ml_ of triisopropylsilanethiol. After heating at reflux for 40 minutes, the reaction mixture was cooled, and 20 ml_ of 2.5 N aqueous sodium hydroxide and 15 ml_ of DMSO were then added under nitrogen. The reaction was stirred vigorously at room temperature for 40 minutes and then diluted into ether. The addition of 125 ml_ of 5% aqueous sodium chloride containing ~5 ml_ of concentrated hydrochloric acid adjusted the pH of the aqueous phase to 4, and the mixture was extracted, separated, extracted the aqueous again with ether, combined the ether extracts, dried with magnesium sulfate, filtered, and concentrated to give a dark liquid. The crude product was diluted into ether, extracted twice with 100-mL portions of 0.5 N aqueous sodium hydroxide (discarded the ether), combined the aqueous extracts, extracted the aqueous solution with ether (discarded ether), carefully adjusted the pH to 3 with concentrated hydrochloric acid, extracted three times with ether, combined the ether extracts, dried with magnesium sulfate, filtered, concentrated, and flash chromatographed on silica gel to give 4.4600 gm of product. 1 H NMR (400 MHz, DMSO-c/e) delta ppm 3.83 (s, 3 H) 5.65 (s, 1 H) 6.36 (d, J=1.95 Hz, 1 H) 7.40 (s, 4 H) 7.44 (d, J=1.95 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 73387-52-7, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-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 73387-52-7, Safety of 5-(4-Bromophenyl)-1-methyl-1H-pyrazole

Step 4: Preparation of 4-(3-{[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide; Scale-Up Alternative; 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (200 g, 0.51 moles), 5-(4-bromophenyl)-1-methyl-1H-pyrazole (126 g, 0.53 moles), and 2-methyltetrahydrofuran (2,000 mL, 10 mL/g of tips carboxamide) were put into the reactor and sparged with nitrogen while heating to 60 C. The sodium methoxide (244.0 mL, 1.07 moles, added as sodium methoxide in methanol solution 25% w/w) was added to the reactor and sparging was continued for another 30 minutes. PdCl2DPPF (3.7 g, 0.005 moles) was added to the reactor and the mixture was heated to 70 C. Once the amount of tips carboxamide was less than 1% of starting amount, the mixture was cooled to 0 C. The mixture was held at 0 C. for one hour. The mixture was filtered and the solid was washed with 2-methyltetrahydrofuran (3×2.5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor and triturated with water (2,000 mL, 10 mL/g) for two hours at 20 C. The mixture was filtered and the solid was washed with water (2,000 mL, 2×5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor with the Si-thiol (90.0 g, 0.5 g/g) and THF (about 12.8 L, 70 mL/g). The mixture was heated to 60-65 C. and held for two hours. The mixture was cooled to 25 C. and filtered. The Si-thiol was washed with THF (about 0.9 L, 5 mL/g). The solution was distilled to a concentration of 10 mL/g. The mixture was cooled to 25 C. and hexanes (422.5 mL, 5 mL/g) was added. The mixture was filtered and the solid was washed with hexanes (422.5 mL, 5 mL/g). The solid was dried in a vacuum oven at 70 C.For 2-methyltetrahydrofuran and water, mL/g are referred to grams of tips carboxamide. For Si-thiol, tetrahydrofuran and hexanes, mL/g are referred to grams of title compound.

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Reference:
Patent; Graneto, Mathew J.; Maddux, Todd M.; Masferrer, Jaime L.; US2008/125474; (2008); 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. 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 73387-52-7

5-(4-bromophenyl)-1 -methyl-1 H-pyrazole (7.84 g), sodium te/f-butoxide (3.81 g), 1 ,1 ‘-bus(di-i-propylphosphino)ferrocene (332 mg), and palladium acetate (148 mg ) were placed under nitrogen and combined with 60 ml_ anhydrous 1 ,4-dioxane. The resulting mixture was stirred at room temperature for 1 hour before adding thisopropylsilanethiol (7.81 ml) followed by heating at reflux for 1 hour. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water twice and 5% aqueous sodium chloride once. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica gel to give the title compound. LCMS (M+H): 347; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 0.85- 0.96 (m, 3 H) 0.96 – 1.02 (m, 18 H) 3.84 (s, 3 H) 7.40 (s, 1 H) 7.46 (s, 1 H) 7.58 (d, J=8.32 Hz, 2 H) 7.63 – 7.71 (m, 2 H).

The synthetic route of 73387-52-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 73387-52-7, These common heterocyclic compound, 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-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.

Step 4: Preparation of 4-(3-{[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide A mixture of 5-(4-bromophenyl)-1-methyl-1H-pyrazole (0.50 g, 2.10 mmols,), 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (0.83 g, 2.10 mmols), Tetrakis(triphenylphosphine)palladium(0) (243 mg, 0.10 equivalents), bis[(2-diphenyl-phosphino)]phenyl ether (113 mg, 0.10 equivalents), and 1.0 M potassium tert-butoxide in THF (6.3 mmols, 3 equivalents) in iPrOH (15 mL) that contained 5% water was heated for 4 hours at 90 degrees Celcius in an atmosphere of nitrogen. The reaction mixture was cooled to room temperature and 7 mL of 1N HCl was added. The product was precipitated by the addition of water (30 mL). The precipitate was collected by suction filtration and washed with water (2*20 mL) and cold ethyl ether (4*20 mL). The tan brown solid was dissolved in a small volume of methylene chloride containing 1% methanol and applied to a 140 g cartridge of silica gel. The cartridge was eluted with an acetone:hexane gradient. The appropriate fractions were concentrated and triturated with methanol to produce a white solid (710 mg) as product. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.75-1.84 (m, 3H) 2.40 (d, J=13.54 Hz, 3H) 3.43-3.51 (m, 1H) 3.72 (d, J=11.34 Hz, 3H) 3.84 (s, 3H) 6.40 (d, J=1.46 Hz, 1H) 7.02 (s, 1H) 7.22-7.30 (m, 2H) 7.34 (d, J=8.05 Hz, 1H) 7.38-7.43 (m, 2H) 7.45-7.52 (m, 3H). HRMS calc M+H, 394.1589, found 394.1630.

Statistics shows that 5-(4-Bromophenyl)-1-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 73387-52-7.

Reference of 73387-52-7, 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. 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

In a 40 ml vial, bromo derivative (236 mg, 1.06 mmol, 1.0 eq.), bispinacolotodiboron (253.6 mg, 1.06 mmol, 1.0 eq.), Pd(dppf)CI2 (86.4 mg, 0.106 mmol, 0.1 eq.) and potassium acetate (321.8 mg, 3.17mmol, 3.0 eq.) were mixed in dioxane (10 ml) and heated to 80 C for 48 hours. LCMS indicated that the product was formed in major amount. . The crude reaction was purified in the presence of silica (10-15 gm) and purified using hexanes: ethyl acetate (0-100%) to yield desired boron ester. Theproduct was characterized by reverse phase HPLC using method 4. (ES, m/z) [M +H+] 284.9. Retention time = 1.42 mins

The chemical industry reduces the impact on the environment during synthesis 5-(4-Bromophenyl)-1-methyl-1H-pyrazole. I believe this compound will play a more active role in future production and life.