Category: 14521-80-3

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. 14521-80-3, name is 3-Bromo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 14521-80-3

Compound 1: 2-(3-(cyclopropylsulfonyl)-1H-pyrazol-1-yl)-N-(5-methoxythiazolo[5,4-b]pyridin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide 3-bromo-1H-pyrazole (1.0 g, 6.8 mmole), NiBr (0.148 g, 0.68 mmole), 2,2′-bipyridine (0.106 g, 0.68 mmole), Zinc dust (0.993 g, 13.6 mmole) and 1,2-dicyclopropyldisulfane (0.993 g, 6.8 mmole) were added to a solution of DMF (20 mL) and the mixture was heated under N2 for 18 h at 80 C. The solvent was removed from the crude reaction mixture under vacuum and the orange gum was treated with MeOH. The resulting ppt was filtered and discarded. Purification of the filtrate with preparative scale HPLC afforded compound 1A as light brown oil (367 mg). [M+H] calc’d for C6H9N2S, 141.04; found 141.0. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.73 (q, J=5.05 Hz, 2H) 1.02-1.17 (m, 2H) 2.26 (ddd, J=7.58, 3.66, 3.41 Hz, 1H) 6.48 (br. s., 1H) 7.82 (br. s., 1H).3-(cyclopropylthio)-1H-pyrazole (1A) (0.083 g, 0.6 mmole) was dissolved in NMP (2 mL) and the solution was chilled to 0 C. NaH (0.060 g, 1.8 mmole) was added and when the reaction subsided methyl 2-bromo-3-(tetrahydro-2H-pyran-4-yl)propanoate (0.060 g, 1.8 mmole) was introduced, and the reaction was heated at 80 C. for 1 h. The reaction was cooled and quenched with a small volume of MeOH and the crude mixture was purified using preparative scale HPLC. Compound 1B as well as a small amount of the carboxylic acid of 1B were collected. Removal of the solvent and treatment of the acid with TMSCH2N2 followed by combination with 1B afforded title compound as oil (81 mg). [M+H] calc’d for C15H23N2O3S (1B ester), 311.14; found 311.0; [M+H] calc’d for C14H21N2O3S (1B acid), 297.12; found 297.0.Compound 1B used directly from the preceding step was treated with Oxone (0.147 g, 0.24 mmole) in a 1:1 solution of THF/H2O (10 mL). After oxidation was judged complete the solvent was removed and the residue was portioned between EtOAc and H2O. The organic layer was separated, dried and concentrated to yield crude compound 1C as oil. This material was purified using preparative scale HPLC and used directly in the next step, [M+H] calc’d for C15H23N2O5S, 343.12; found 343.3.5-Methoxythiazolo[5,4-b]pyridin-2-amine (0.048 g, 0.26 mmole) was added to a microwave vial followed by DCE (2 mL). The reaction mixture was cooled to 0 C. under a N2 atmosphere. Trimethyl aluminum (2M in hexanes) (0.13 mL, 0.26 mmole) was added and when the reaction subsided the cooling bath was removed, the solution was then stirred at RT for 15 min. To this was added a solution of methyl 2-(3-(cyclopropylsulfonyl)-1H-pyrazol-1-yl)-3-(tetrahydro-2H-pyran-4-yl)propanoate 1C (0.015 g, 0.04 mmole) in DCE (2 mL) and the reaction mixture was heated in a microwave at 110 C. for 1 h. The reaction was then quenched with 1N HCl and extracted 2× with DCM. The organic layers were pooled, dried over Na2SO4; the solvent was removed and the crude residue was purified by preparative scale HPLC to afford compound 1 (46 mg). [M+H] calc’d for C21H26N5O5S2, 492.13; found 492.0. 1H NMR (400 MHz, MeOD) delta ppm 1.07 (dd, J=7.96, 2.15 Hz, 2H) 1.18-1.42 (m, 6H) 1.52 (d, J=9.35 Hz, 1H) 1.74 (d, J=2.02 Hz, 1H) 2.14 (t, J=6.32 Hz, 1H) 2.32 (t, J=10.48 Hz, 1H) 2.61-2.80 (m, 1 H) 3.29 (m, 1H, under MeOD signal) 3.79-3.98 (m, 5H) 5.50 (ddd, J=10.80, 5.68, 5.49 Hz, 1H) 6.81-6.90 (m, 2H) 7.94 (d, J=8.84 Hz, 1H) 8.10 (d, J=2.53 Hz, 1H)

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

Reference:
Patent; TAKEDA SAN DIEGO, INC.; US2009/286800; (2009); 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., HPLC of 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

Electric Literature 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.

23a 3-Bromo-l-(4-nitrophenyl)-l /-pyrazole 23a: Sodium hydride (60% w/w in mineral oil, 41 mg, 1.02 mmol, 1.5 equiv) was carefully added in portions to a stirred solution of 22a (100 mg, 0.68 mmol, 1.0 equiv) in THF (6.8 mL) at 0 C. After 20 min, 1-fluoro -4 -nitrobenzene 22c (0.08 mL, 0.75 mmol, 1.1 equiv) was added dropwise, and the reaction mixture was set to reflux at 60 C. Upon consumption of the starting material as indicated by TLC, the reaction mixture was cooled to 25 C, quenched with a saturated solution of aqueous ammonium chloride (1.2 mL), and the two phases were separated. The aqueous layer was extracted with ethyl acetate (3 x 5 mL), and the combined organic layers were dried with anhydrous magnesium sulfate and concentrated in vacuo. The crude residue obtained was purified by flash column chromatography (silica gel, 20% ethyl acetate in hexanes) to afford -arylpyrazole 23a (144 mg, 0.54 mmol, 79%) as a white solid. 23a: Rf = 0.30 (silica gel, 20% ethyl acetate in hexanes); FT-IR (neat) v 3144, 1595, 1516, 1407, 1359, 1335, 1200, 1176, 1112, 1042, 955, 937, 852, 749, 732, 684 cm 1; NMR (600 MHz, CDC13) delta = 8.33 (d, J = 9.2 Hz, 2 H), 7.93 (d, J = 2.6 Hz, 1 H), 7.84 (d, J = 9.2 Hz, 2 H), 6.58 (d, J = 2.6 Hz, lH) ppm; 13C NMR (151 MHz, CDC13) delta = 145.9, 143.7, 130.7, 129.0, 125.6, 118.6, 112.6 ppm; HRMS (ESI) calcd for C9H6BrN302 [M+H]+ 267.9716 found 267.9711.

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

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.

Step 5. Synthesis of N-[3-({4-[2-(3-bromo-lH-pyrazol-l-yl)-l,l,l,3,3,3-hexafluoropropan~ 2-yl]-2,6-dimethylphenyl}carbamoyl)phenyl]-2-chloropyridine-3-carboxamide.; 2-(4- { [(3 – { [(2-chloropyridin-3 -yl)carbonyl]amino } phenyl)carbonyl]amino } -3 ,5 -dimethylphenyl)- 1 ,l,l,3,3,3-hexafluoro-2-yl methanesulfonate (0.10 g) and 3-bromopyridine (28 mg) were dissolved in DMF (1.5 ml), and sodium hydride (in oil, 10 mg) was added thereto under ice cooling. After stirring for 4 hours, water was added. The resulting mixture was extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. After the filtration, the solvent was evaporated off under reduced pressure. The resulting residue was purified with silica gel chromatography to obtain the title compound (76 mg, 70%).1H-NMR (CDCl3) delta : 2.31(6H, s), 6.45 (IH, d), 7.16 (2H, s), 7.36-7.64 (4H, m), 7.74 (IH, d), 7.86 (IH, d), 8.14-8.22 (IH, m), 8.29 (IH, s), 8.44-8.55 (2H, m).

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

Related Products of 14521-80-3, The chemical industry reduces the impact on the environment during synthesis 14521-80-3, name is 3-Bromo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

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-l-yl)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 59”).Active compound 591H-NMR (CDC13) 6: 8.92 (s, IH), 8.89 (d, J=5.1 Hz, IH), 8.16 (d, J=5.1 Hz, IH), 8.08-8.07 (m, IH), 7.69 (dd, J=8.8, 1.2 Hz, IH), 7.66 (d, J=2.4 Hz, IH), 7.59 (d, J=8.8 Hz, IH), 6.57 (d, J=2.4 Hz, IH)

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, 3-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Electric Literature 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: In a150 mL pressure vessel, a suspension of 3-bromo-1H-pyrazole (8 g, 54.43 mmol) cesiumcarbonate (53.2 g, 163.29 mmol), and difluoroiodomethane (10% wt. in THF, 200 ml, 106.23mmol) was heated at 45C overnight. The reaction mixture was cooled to room temperature andthen filtered through Celite. The filter cake was washed with Et20 (3 x 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), butyldi- 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 mm 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 Na2504, filtered and concentratedunder reduced pressure. The crude residue was purified by silica column chromatography (5% to15% EtOAc/Hex). Mixed fractions were recrystallized (5:1 Hex/EtOAc) combined pure product afforded P4. 1HNMR (400 MHz, Chloroform-d) oe 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).

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.

Adding a certain compound to certain chemical reactions, such as: 14521-80-3, name is 3-Bromo-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 14521-80-3, HPLC of Formula: C3H3BrN2

Step A: Preparation of methyl N-[[5-(3-bromo- lH-pyrazol- 1 -yl)-2- methylphenyljmethyl] carbamate 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).

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.

These common heterocyclic compound, 14521-80-3, name is 3-Bromo-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. HPLC of Formula: C3H3BrN2

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 ¡Á 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The synthetic route of 3-Bromo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Application of 14521-80-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 14521-80-3 name is 3-Bromo-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 3-bromo-1H-pyrazole (5.39 g, 36.67 mmol) and triphenylchloromethane (10.40 g, 37.41 mmol) in DCM (300 ml) was added trimethylamine (7.41 g, 73.37 mmol). The reaction mixture was heated at 50 00 for 18 hours (overnight). After this time, the mixture was concentrated under reduced pressure and chromatographed [Si02] to give 3-bromo-1-trityl-pyrazole (P17) (8.97 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-1H-pyrazole, and friends who are interested can also refer to it.

Electric Literature of 14521-80-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 14521-80-3 as follows.

To a solution of 3-bromo-1H-pyrazole (10 g, 68.0 mmol) in H2SO4 (50 mL) was added HNO3 (10.7 g, 170 mmol) at 0-10 C. Then, the mixture was stirred at 80 C. for 2 hours. On completion, the mixture was cooled to 25 C. Then, the mixture was poured into ice/water (300 mL), then extracted with EA (3¡Á150 mL). The combined organic layer was washed with sat. aq. NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give the title compound (11.2 g, 85% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 8.94 (s, 1H).

According to the analysis of related databases, 14521-80-3, the application of this compound in the production field has become more and more popular.