Category: 14521-80-3

14521-80-3, 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-1H-pyrazole obtained in Step C of Example 6 (600 mg) in N,N-dimethylformamide (40 mL) was added potassium tert-butoxide tetrahydrofuran solution (1 M, 6.12 mL) at room temperature, and the mixture was stirred for 10 min. To the reaction mixture was added 1-chloro-2-(methylsulfonyl)ethane obtained in Step A (873 mg) at room temperature, and the mixture was stirred for 2 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (730 mg). 1H NMR (400 MHz, CDCl3) delta 2.57 (3H, s), 3.63 (2H, t, J = 6.2 Hz), 4.58 (2H, t, J = 6.2 Hz), 6.30 (1H, d, J = 2.0 Hz), 7.43 (1H, d, J = 2.0 Hz)

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Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H3BrN2

Reference Production Example 4; (1) A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 ml of N,N-dimethylformamide was stirred at 100C for 8 hours. After the reaction mixture was cooled to room temperature, water was poured into the reaction mixture. The reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

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 14521-80-3.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2143720; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

14521-80-3, name is 3-Bromo-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. HPLC of Formula: C3H3BrN2

Step C: Preparation of 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridineTo a mixture of 2,3-dichloropyridine (27.4 g, 185 mmol) and 3-bromopyrazole (i.e. the product of Step B) (25.4 g, 176 mmol) in dry N,N-dimethylformamide (88 mL) was added potassium carbonate (48.6 g, 352 mmol), and the reaction mixture was heated to 125 C. for 18 hours. The reaction mixture was cooled to room temperature and poured into ice water (800 mL). A precipitate formed. The precipitated solids were stirred for 1.5 hrs, filtered and washed with water (2×100 mL). The solid filter cake was taken up in methylene chloride and washed sequentially with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic extracts were then dried over magnesium sulfate and concentrated to afford 39.9 g of a pink solid. The crude solid was suspended in hexane and stirred vigorously for 1 hr. The solids were filtered, washed with hexane and dried to afford the title product as an off-white powder (30.4 g) determined to be >94% pure by NMR. This material was used without further purification in Step D. 1H NMR (CDCl3) delta 6.52 (s, 1H), 7.30 (dd, 1H), 7.92 (d, 1H), 8.05 (s, 1H), 8.43 (d, 1H).

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E I DU PONT DE NEMOURS AND COMPANY; Lahm, George Philip; McCann, Stephen Frederick; Patel, Kanu Maganbhai; Selby, Thomas Paul; Stevenson, Thomas Martin; US9113630; (2015); B2;,
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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-1H-pyrazole

Example 9. Synthesis of 4-(3-(3-oxa-9-azaspiro[5.5]undecan-9-yl)-lH-pyrazol-l- yl)-2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one, 1-9 Synthesis of compound 9.2. To a mixture of 1.4 (0.4g, 1.05mmol, l .Oeq) in 1 ,4- dioxane (5.0 ml) was added 3-Bromo-lH-pyrazole (0.169g, 1.15mmol, 1.1 eq) and K2CO3 (0.29g, 2.10mmol, 2.5eq). The reaction mixture was degassed for 10 min. under argon atmosphere, then Pd2(dba)3 (0.096 g, 0.01 mmol, O. leq) and Xantphos (0.121g, 0.2mmol, 0.2eq) were added, and again degassed for 5 min. The reaction was then heated at 100 C for 2 h. Upon completion of the reaction, reaction mixture was poured into water and product was extracted with EtOAc. Organic layers were combined, washed with brine solution, dried over Na2S04 and concentrated under reduced pressure to obtain crude which was purified by column chromatography to provide 9.2 (0.1 1 g, 21.4%). MS(ES): m/z 9 [M+H]+.

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; MONDAL, Sayan; (342 pag.)WO2017/40757; (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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-1H-pyrazole

A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 mL of N,N-dimethylformamide was stirred at 100C for 8 hours. After cooling to room temperature and adding water, the reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

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; Sumitomo Chemical Company, Limited; EP2145885; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14521-80-3,Some common heterocyclic compound, 14521-80-3, name is 3-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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: Pyrazoles 4 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and NBS or NIS (1.5 mmol) were dissolved in 2 mL of EtOAc solvent. the reaction mixture was stirred at room temperature under air for 12 h. After the reaction, the resulting mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and the solvent was then removed under vacuum. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to afford the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-1H-pyrazole, its application will become more common.

Reference:
Article; Fu, Lili; Bao, Xiaodong; Li, Shanshan; Wang, Lingtian; Liu, Zhiguo; Chen, Wanzhi; Xia, Qinqin; Liang, Guang; Tetrahedron; vol. 73; 17; (2017); p. 2504 – 2511;,
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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3BrN2

Production Example 60 A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.19 g of 3-bromopyrazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.31 g of 2-[3-(3-bromopyrazole-1-yl)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 59”). [Show Image] 1H-NMR (CDCl3) delta: 8.92 (s, 1H), 8.89 (d, J=5.1 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 8.08-8.07 (m, 1H), 7.69 (dd, J=8.8, 1.2 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7. 59 (d, J=8.8 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H)

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

14521-80-3, name is 3-Bromo-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. category: pyrazoles-derivatives

Methyl N-[(2-methyl-5-iodophenyl)methyl]carbamate (i.e. the product of Example 3, Step C) (5.00 g, 16.4 mmol), 3-bromopyrazole (3.11 g, 21.3 mmol), potassium carbonate (5.65 g, 41.0 mmol), and copper (I) iodide (623 mg, 3.28 mmol) were combined in toluene (16 mL) and N,N’-dimethylformamide (16 mL). A stream of nitrogen gas was bubbled into the mixture for 30 min., N,1ST -dimethyl- 1 ,2-cyclohexanediamine (1.0 mL, 6.6 mmol) was added and a stream of nitrogen gas was bubbled through the mixture for an additional 30 min. The nitrogen line was then raised above the reaction mixture and the mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered through a fritted- glass funnel and then concentrated under vacuum. The resultant residue was purified by medium pressure liquid chromatography using a gradient of 10 to 50% ethyl acetate in hexanes to provide the title compound (4.35 g) as an off- white solid. in NMR (500 MHz, CDC13) delta 7.76 (d, J=2.5 Hz, 1 H), 7.55 (d, J=2.0 Hz, 1 H), 7.42 (dd, J=8.1, 2.0 Hz, 1 H), 7.23 (d, J=8.2 Hz, 1 H), 6.45 (d, J=2.6 Hz, 1 H), 5.00 (bs, 1 H), 4.40 (d, J=5.7 Hz, 2 H), 3.71 (s, 3 H), 2.34 (s, 3 H).

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; TAGGI, Andrew, Edmund; DIETRICH, Robert, F.; MARCUS, Kimberly, Katherine; MCCANN, Stephen, Frederick; WO2014/66120; (2014); 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

1.1 Synthesis of Intermediates P Synthesis of 4-(1-(difluoromethyl)-1H-pyrazol-3-yl)-2, 6-difluorobenzaldehyde (P4) In a 150 mL pressure vessel, a suspension of 3-bromo-1H-pyrazole (8 g, 54.43 mmol) cesium carbonate (53.2 g, 163.29 mmol), and difluoroiodomethane (10% wt. in THF, 200 mL, 106.23 mmol) was heated at 45 C. overnight. The reaction mixture was cooled to room temperature and then filtered through Celite. The filter cake was washed with Et2O (3*150 mL). The filtrate was washed with brine, dried over sodium sulfate and carefully concentrated (20 C. bath, 100 mb vacuum) to give ?17 g of a 1.5:1 ratio of regioisomers and solvent still present. This crude material was combined with 3,5-difluoro-4-formylphenylboronic acid (12.65 g, 68.03 mmol), palladium acetate (0.31 g, 1.381 mmol), butyl di-1-adamantylphosphine (1.171 g, 3.265 mmol) and potassium carbonate (22.80 g, 164.96 mmol) in dioxane (150 mL) and water (50 mL) the mixture was degassed for 10 min with argon, then heated at 100 C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduce pressure, the residue was diluted with EtOAc and washed with brine 2x then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (5% to 15% EtOAc/Hex). Mixed fractions were recrystallized (5:1 Hex/EtOAc) and the combined pure product afforded P4. 1H NMR (400 MHz, Chloroform-d) delta 10.35 (d, J=1.0 Hz, 1H), 7.92 (d, J=2.8 Hz, 1H), 7.46 (d, J=9.6 Hz, 2H), 7.24 (t, J=60.5 Hz, 1H), 6.80 (d, J=2.8 Hz, 1H).

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; Gilead Sciences, Inc.; Chin, Elbert; Kato, Darryl; Link, John O.; Shapiro, Nathan; Yang, Zheng-Yu; (81 pag.)US2020/30327; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 14521-80-3, 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-bromopyrazole (1.00 g, 6.8 mmol) in ethyl ether (20 mL) was treated with 37% formaldehyde (0.3 mL, 4.0 mmol). The obtained solution was set aside at room temperature overnight. The volatiles were evaporated under reduced pressure. Toluene (5 mL) was added, and the evaporation was repeated. The obtained oil was triturated with ethyl ether (3 mL) to crystallize. The crystals were separated by decantation and dried to give 3-bromo-l- (hydroxymethyl)pyrazole (371 mg, 37%). A suspension of the obtained product in chloroform (5 mL) was treated with thionyl chloride (0.5 mL) and heated at reflux for 1 h. The volatiles were removed under reduced pressure to provide crude 3-bromo-l-(chloromethyl)pyrazole. A suspension of the unsubstituted triazinone from Example 38 (100 mg, 0.41 mmol) in DMF (3 mL) was treated with 60% NaH (18 mg, 0.45 mmol) followed by 3-bromo-l- (chloromethyl)pyrazole (82 mg, 0.49 mmol). After stirring for 1 h at room temperature, the solvent was evaporated under reduced pressure, and the residue was chromatographed (chloroform/ethyl acetate, 1 : 1). The obtained material was recrystallized from ethanol (5 mL) to give the desired product, 70 mg, MP: 180-1810C. 1H NMR (CDCl3) delta 2.03 (1 H, m), 2.19 (1 H, m), 2.35 (1 H, m), 2.53 (1 H, m), 3.70 (1 H, m), 3.91 (1 H, dt, J = 12.3 and 7.2 Hz), 5.61 (1 H, t, J = 6.0 Hz), 6.55 ( 1 H, d, J = 13.8 Hz), 6.60 (1 H, d, J = 13.5 Hz), 7.51 (1 H, s), 7.85 (1 H, s), 7.87 (1 H, s), and 8.77 (1 H, s).

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

Reference:
Patent; CORTEX PHARMACEUTICALS, INC.; WO2008/85505; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics