Category: 15366-34-4

Reference of 15366-34-4, These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 mixture of 3-[5-(bromomethyl)-2-thienyl]-5-(trifluoromethyl)-1 ,2,4-oxadiazole (1.0 g, 3.2 mmol), methyl 1 H-pyrazole-3-carboxylate (600 mg, 4.8 mmol) and potassium carbonate (880 mg, 6.4mmol) in acetonitrile (32 mL) was heated at 1 10C for 2 hours. The orange suspension was filtered to remove the solids and the filtrate solution was then concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography on silica gel using a cyclohexane/ethyl acetate gradient to afford 610 mg of the title compound as a white solid. LC/MS (Method A) retention time = 1.00 minutes, 359 (M+H). 1NMR (400 MHz, CDCI3) delta ppm: 7.78 (d, 1 H), 7.51 (d, 1 H), 7.12 (d, 1 H), 6.89 (d, 1 H), 5.61 (s, 2H), 3.98 (s, 3H). methyl 2-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-3-carboxylate (Compound 1.54 of Table T1 ) was isolated as a byproduct in form of a white solid (274 mg). LC/MS (Method A) retention time = 1.10 minutes, 359 M+H).

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; PITTERNA, Thomas; RAJAN, Ramya; (0 pag.)WO2018/158365; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 15366-34-4, Recommanded Product: 15366-34-4

Methyl 1H-pyrazole-3-carboxylate (0.500 g, 3.96 mmol) was dissolved in dry MeCN (30 mL), then (bromomethyl)cyclopropane (0.46 1 mL, 4.76 mmol) was added,followed by cesium carbonate (1.94 g, 5.95 mmol). The reaction mixture was stirred at 60C for 2 h. The reaction mixture was cooled to rt and diluted with EtOAc. ThenCELITE was added, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (solid loading on CELITE, 0-55% EtOAc/Hex) affording two products.Intermediate hA (0.197 g, 28% yield) as a colorless syrup eluted at 20%EtOAc. MS(ESI) m/z: 180.9 (M+H) ?HNMR: (500 MHz, CDC13) oe ppm 7.49 (d, J1.9 Hz, 1H), 6.84 (d, J=1.9 Hz, 1H), 4.44 (d, J=7.2 Hz, 2H), 3.88 (s, 3H), 1.44 – 1.31 (m,1H), 0.57 – 0.48 (m, 2H), 0.45 – 0.37 (m, 2H).Intermediate 12A (0.4 15 g, 58% yield) as a colorless syrup eluted at 42%EtOAc. MS(ESI) m/z: 180.9 (M+H) ?H NMR: (500 MHz, CDC13) oe ppm 7.54 (d, J2.5Hz, 1H), 6.84 (d, J=2.5 Hz, 1H), 4.07 (d, J=7.2 Hz, 2H), 3.93 (s, 3H), 1.32 (quint, J7.6,4.9 Hz, 1H), 0.71 – 0.64 (m, 2H), 0.45 – 0.36 (m, 2H).

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

These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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. Recommanded Product: 15366-34-4

To a solution of A/-(2-bromophenyl)quinolin-3-amine (164 mg, 0.55 mmol) in DMF (2.5 mL), were added methyl 7/- -pyrazole-3-carboxylate (63 mg, 0.50 mmol), copper(l) iodide (10 mg, 0.05 mmol), L- proline (12 mg, 0.10 mmol) and potassium phosphate (212 mg, 1.0 mmol). The mixture was stirred at 120 C for 18 h. The crude mixture was purified by preparative HPLC (CH3CN/H2O) to afford the title compound as a yellow solid (80 mg, 42%). LogP = 2.16 [Method A]. Mass (M+H) = 345. Purity = 99% (LC-210nm).

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

Adding a certain compound to certain chemical reactions, such as: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 15366-34-4, Recommanded Product: 15366-34-4

Methyl 1 H-pyrazole-3-carboxylate (12.61 mg, 0.1 mmol) was dissolved in a 0. 105M solution of potassium tert-butoxide in ethanol (1 ml, 11.78 mg, 0.105 mmol). After stirring at room temperature for 5 mins, a 0. 1 M solution of 4-bromo-2- (bromomethyl) phenyl phenylmethyl ether in ethanol (1 ml, 35.6 mg, 0.1 mmol) was added and the resulting solution was stirred and heated at 60C under nitrogen for 4hrs. After cooling the mixture was diluted with ethanol (1 ml) and a 0.5M solution of lithium hydroxide in water (1 ml, 11.97mg, 0. 5mmol) was added. The mixture was stirred overnight at 40C. After cooling 2M hydrochloric acid (0. 3moi, 0. 6mmol) was added and the mixture was diluted with water. Dichloromethane was added and the mixture stirred vigorously. The organic layer was separated and the solvent removed in vacuo. The residue was purified by mass directed autopurification to yield the title compound. 1-({5-bromo-2-[(phenylmethyl) oxy] phenyl} methyl)-5-methyl-1 H-pyrazole-3-carboxylic acid: (10. 7mg, 27.6%). ‘H NMR 8 : 5.08 (2H, s), 5.34 (2H, s), 6.72 (1H, d, J = 2.2Hz), 6.92 (1H, d, J = 8.8Hz), 7.23 (1H, d, J = 2Hz), 7.30-7. 39 (6H, m), 7.45 (1H, d, J = 2Hz). t = 3.38, [MH+] 387, 389 [MH-] 385,387.

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

Electric Literature of 15366-34-4, 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. 15366-34-4 name is Methyl 1H-pyrazole-3-carboxylate, 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.

Step 4: To a mixture of methyl 1H-pyrazole-5-carboxylate (3.15 g, 25.0 mmol), cyclopropylboronic acid (4.30 g, 50.0 mmol), sodium carbonate (5.30 g, 50.0 mmol), and dichloroethane (125 mL) at 70 C was added a heated suspension of copper(II) acetate (4.55 g, 25.0 mmol), 1,10-phenanthroline (4.50 g, 25.0 mmol), and dichloroethane (31 mL). The reaction mixture was then stirred vigorously under air at 70 C for 4 hours. The reaction mixture was cooled and filtered through Celite. The solvent was removed and the residue purified by silica gel chromatography (0 to 100% EtOAc in hexanes) to afford the desired product as a pale green

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

15366-34-4, Adding some certain compound to certain chemical reactions, such as: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 15366-34-4.

To a solution of 6-chloro-4-methyl-2-phenylbenzo[d]thiazole (24, 300mg, 1.15mmol) in tetrachloromethane (7.5mL) were added N-bromosuccinimide (246mg, 1.39mmol) and azoisobutyronitrile (19.0mg, 0.115mmol) at room temperature, and the mixture was stirred at reflux temperature for 8h. After cooling to room temperature, saturated aq. sodium thiosulfate and saturated aq. sodium bicarbonate were added to the mixture. The mixture was extracted with diethyl ether. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt=1:1) to give 4-(bromomethyl)-6-chloro-2-phenylbenzo[d]thiazole. Meanwhile, in a separate flask, sodium hydride (38.0mg, 0.799mmol, 60% oil suspension) was added to a solution of ethyl 5-methyl-1H-pyrazole-3-carboxylate (82.1mg, 0.530mmol) in DMF (0.9mL) at 0C. After the mixture was stirred at room temperature for 10min, 4-(bromomethyl)-6-chloro-2-phenylbenzo[d]thiazole was slowly added at 0C. After stirring at 0C for 0.5h, saturated aq. ammonium chloride was added to the mixture. The mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, then dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt=2:1) to give the title compound 25 as a colorless solid (53.0mg, 11%).

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 15366-34-4.

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 15366-34-4 as follows. 15366-34-4

A mixture of 3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1 ,2,4-oxadiazole (5.0 g, 16.3 mmol), methyl 1 H-pyrazole-3-carboxylate (3.08 g, 24.4 mmol) and potassium carbonate (3.29 g, 32.5 mmol) in acetonitrile (81 mL) was heated at 25C for 4 hours. The white suspension was filtered to remove the solids and the filtrate solution was then concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography on silica gel (cyclohexane:ethyl acetate eluent gradient 99:1 to 35:65) to afford 3.90 g of the title compound as a white solid. LC/MS (Method A) retention time = 1.02 minutes, 353 (M+H). (0725) NMR (400 MHz, CDCI3) delta ppm: 8.12 (d, 2H), 7.49 (d, 1 H), 7.39 (d, 2H), 6.89 (s, 1 H), 5.51 (s, 2H), 3.98 (s, 3H). methyl 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-3-carboxylate (Compound 5.2 of Table T5) was isolated as a byproduct in form of a white solid (1.53 g). LC/MS (Method A) retention time = 1 .1 1 minutes, 353 (M+H). (0726) NMR (400 MHz, CDCIs) delta ppm: 8.05 (d, 2H), 7.55 (s, 1 H), 7.40 (d, 2H), 6.95 (s, 1 H), 5.35 (s, 2H), 3.85 (s, 3H).

According to the analysis of related databases, 15366-34-4, the application of this compound in the production field has become more and more popular.

These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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. 15366-34-4

A mixture of methyl liT-pyrazole-3-carboxylate (500.0 mg, 3.96 mmol), 3- methoxyphenyl boronic acid (901.0 mg, 5.9 mmol), Cu(OAc)2 (1.43 g, 7.9 mmol) and TEA (2.7 mL, 19.7 mmol) in DCM (15 mL) was stirred at 40 C for 12 h under 02 atmosphere. The reaction mixture was then filtered. The filtrate was concentrated, and the residue was purified by flash silica gel chromatography (80 g column, EtOAc in petroleum ether from 0% -30%) to give methyl l-(3-methoxyphenyl)-liT-pyrazole-3-carboxylate (190 mg, 21% yield, the higher polarity) as a yellow oil ( LC-MS (ESI+) m/z: 232.9 (M+H)+) and methyl l-(3-methoxyphenyl)-liT-pyrazole-5-carboxylate (30.0 mg, 3% yield) as a yellow solid( LC-MS (ESI+) m/z: 232.9 (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 15366-34-4.

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 15366-34-4 as follows. 15366-34-4

a) Methyl 1-(2-methylprop-1-enyl)-1H-pyrazole-3-carboxylate The title compound was prepared using the procedure described in Example 17(a) starting from methyl 1H-pyrazole-3-carboxylate (8 g, 63.4 mmol) and 1-bromo-2-methyl propene (12.7 g, 95.2 mmol). The product was purified with flash chromatography. Yield 2.4 g. 1H-NMR (400 MHz; CDCl3): delta 1.81 (d, 3H), 1.87 (d, 3H), 3.93 (s, 3H), 6.70 (d, 1H), 6.87 (d, 1H), 7.47 (d, 1H).

According to the analysis of related databases, 15366-34-4, the application of this compound in the production field has become more and more popular.

15366-34-4, A common compound: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Methyl 1H-pyrazole-3-carboxylate (0.500 g, 3.96 mmol), was dissolved in DCE (25 mL), then cyclopropylboronic acid (0.681 g, 7.93 mmol) and sodium carbonate(0.840 g, 7.93 mmol) were added. The reaction mixture was heated to 70 C, and then a mixture of 2,2?-bipyridine (0.6 19 g, 3.96 mmol) and copper(II) acetate (0.720 g, 3.96 mmol) were added in one batch. The reaction mixture was stirred at 70 C under oxygen atmosphere (1 atm) for 2 d. Saturated aq. NaHCO3 solution was added to the reaction mixture, and it was extracted with EtOAc (3x). The combined organic phase was concentrated. The residue was purified by flash chromatography (solid loading on CELITE, 0-65% EtOAc/Hex) affording two products.Intermediate 15A (0.119 g, 18% yield) as a colorless syrup eluted at 2O% EtOAc. MS(ESI) m/z: 167.0 (M+H) ?H NMR: (400 MHz, DMSO-d6) oe ppm 7.40 (d,J=2.0 Hz, 1H), 6.82 (d, J=2.0 Hz, 1H), 4.31 -4.24 (m, 1H), 2.11 (s, 3H), 1.29- 1.22 (m,2H), 1.10- 1.00 (m, 2H).Intermediate 16A (0.37 1 g, 56% yield) as a colorless syrup eluted at 45% EtOAc. MS(ESI) m/z: 167.0 (M+H) ?H NMR: (400 MHz, DMSO-d6) oe ppm 77.46 (d, J=2.4 Hz, 1H), 6.78 (d, J=2.2 Hz, 1H), 3.92 (s, 3H), 3.67 (tt, J=7.4, 3.9 Hz, 1H), 1.23 -1.15 (m, 2H), 1.09- 1.01 (m, 2H).

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