Month: October 2020

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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., 25016-11-9

103a) (E)-tert-Butyl 3-(1 -methyl-1 H-pyrazol-4-yl)acrylate To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (12.60 g, 49.9 mmol) in tetrahydrofuran (THF) (30 mL) was added NaH 60% dispersion in mineral oil (2.179 g, 54.5 mmol) slowly. The mixture was stirred for 10 min at room temperature. A solution of 1 -methyl-1 H-pyrazole-4-carbaldehyde (5.0 g, 45.4 mmol) in tetrahydrofuran (THF) (30 mL) was added slowly. After addition, the reaction mixture was stirred for 20 min at room temperature. The LCMS showed a complete reaction. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous MgSCv It was filtered and the filtrate was concentrated to give the crude product which was then purified on the Combiflash column chromatography eluting with a gradient of 0 to 50% ethyl acetate in hexanes. The title compound was obtained as clear colorless oil (9.0 g, 43.2 mmol, 95 % yield). LC-MS m/z 208.9 (M+H)+, 0.93 min (ret. time).

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.

83-10-3, 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. 83-10-3 name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, 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) N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80 C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0 C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). MS (ESI, pos. ion) m/z: 376.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta (ppm) 2.68 (s, 3H), 3.34 (s, 3H), 7.02-7.04 (d, J=8.8 Hz, 1H), 7.41-7.43 (m, 2H), 7.48-7.52 (m, 1H), 7.56-7.60 (m, 2H), 829-8.33 (d, J=13.8 Hz, 1H), 10.08 (s, 1H), 10.95 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

288-13-1, 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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below.

The acetic anhydride and fuming nitric acid are slowly mixed in an ice water bath at a volume ratio of 5.5:1 to obtain a nitrating agent, and the nitratingagent and the pyrazole acetic acid solution are respectively delivered to the microchannel reactor through a high-pressure constant-flow pump with precise flow control. The twoinlets control the molar ratio of nitric acid to pyrazole to be 1.1:1. At 45-70 ¡ãC, the two liquids are instantaneously mixed in the microchannel reactorand reacted. The reaction solution is poured into crushed ice and filtered. It was washed with ice water and dried under vacuum to give N-nitropyrazole; theflow rate of the acetic acid solution of the pyrazole was 0.1 mL/min.The yield and purity of N-nitropyrazole are shown in Table 1 and Figure 2.

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.

5334-43-0, 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 5334-43-0 as follows.

EXAMPLE 3 1-Phenyl-4-cyano-5-(dicyclohexylaminosulfonylureido)pyrazole STR108 4.4 ml (50 mmol) of chlorosulfonyl isocyanate were added to a solution of 9.2 g (50 mmol) of 1-phenyl-4-cyano-5-aminopyrazole in 100 ml of methylene chloride. Stirring was carried out for 30 minutes at about 20 C., after which a solution of 7.5 ml (60 mmol) of triethylamine and 10 ml (50 mmol) of dicyclohexylamine in 50 ml of methylene chloride was slowly added dropwise. After the end of the addition, stirring was continued for a further hour and hydrolysis was then carried out with 200 ml of water. The organic phase was separated off and was worked up in a conventional manner to give the product. Yield: 87%.

According to the analysis of related databases, 5334-43-0, the application of this compound in the production field has become more and more popular.

A common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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. 4522-35-4.

l-(But-3-en-l-yl)-3-iodo-lH-pyrazole. To a solution of 5-iodo-lH-pyrazole (1.34 g, 6.91 mmol, 1 equiv) in DMF (23 mL) was added 60% NaH (0.33 g, 8.29 mmol, 1.2 equiv). After 10 min, 4-bromobut-l-ene (0.84 mL, 8.29 mmol, 1.2 equiv) was added. After stirring 3 d, the reaction was added to water and extracted with EtOAc (x3). The combined EtOAc extracts were dried (Na2S04) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100%) EtOAc in hexane) to provide a 3: 1 mixture of product isomers (1.12 g, 65%>) as a colorless oil. Major isomer: 1H NMR (400 MHz, CDC13) delta 7.21 (d, J= 2.3 Hz, 1H), 6.39 (d, J= 2.3 Hz, 1H), 5.80 – 5.68 (m, 1H), 5.13 – 5.05 (m, 2H), 4.20 (t, J= 7.2 Hz, 2H), 2.61 (qt, J= 7.0, 1.3 Hz, 2H). Minor isomer: 1H NMR (400 MHz, CDC13) 7.53 (d, J= 1.8 Hz, 1H), 6.42 (d, J= 1.8 Hz, 1H), 5.81 (ddt, J= 17.1, 10.2, 6.9 Hz, 1H), 5.14 – 5.05 (m, 2H), 4.27 (t, J= 7.3 Hz, 2H), 2.65 – 2.58 (m, 2H).

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

25222-43-9, A common compound: 25222-43-9, name is (1H-Pyrazol-4-yl)methanol, 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.

A mixture of (5S,7S)-2-bromo-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[l,2-b] [l,2,4]triazole (300 mg, 1.06 mmol), copper(l) iodide (1064 mg, 10.63 mmol), (lSSj-N lS -dimethylcyclohexane-l- diamine (1210 mg, 8.51 mmol), cesium carbonate (1039 mg, 3.19 mmol) and (lH-pyrazol-4- yl)methanol (1064 mg, 10.63 mmol) in 1,4-dioxane (2.5 mL) was heated at 140 ¡ãC for 3h a sealed tube under microwave. After cooled, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 15percent MeOH in isopropyl acetate) to afford final product (169 mg, 53percent) as a white solid. LC-MS T = 0.92 min, m/z = 300.1 (M+H) +. LCMS (5 to 95percent acetonitrile in water + 0.1percent formic acid over 2 mins) retention time 0.92 min, ESI+ found [M+H] = 300.1

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, (1H-Pyrazol-4-yl)methanol, other downstream synthetic routes, hurry up and to see.

A common compound: 28466-26-4, name is 4-Aminopyrazole, 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. 28466-26-4

10054] A 250-mE 3-neck flask was charged with 1H-pyra- zol-4-amine (5 g, 60.2 mmol) and dichioromethane (50 mE). The resulting suspension was cooled to 5 C. and triethylamine (9.13 g, 90.0 mmol) was added, followed by acetic anhydride (7.37 g, 72.2 mmol) at <20 C. The reaction was stirred at room temperature for 18 hours, at which point thin layer chromatography [Eluent: ethyl acetate] analysis indicated that the reaction was incomplete. Additional triethylamine (4.57 g, 45.0 mmol) and acetic anhydride (3.70 g, 36.0 mmol) were added and the reaction was heated at 30 C. for an additional 3 hours to give a dark solution, at which point thin layer chromatography analysis indicated that only a trace of starting material remained. The reaction mixture was purified by flash column chromatography using ethyl acetate as eluent. The fractions containing pure product were combined and concentrated to dryness to afford an off-white solid. The solid was dried under vacuum at room temperature for 18 hours (5.55 g, 55%): ?H NMR (400 MHz, DMSO-d5) oe 10.30 (s, 1H), 8.39 (d, J=0.7 Hz, 1H), 7.83 (d, J=0.7 Hz, 1H), 2.60 (s, 3H), 2.03 (s, 3H); ElMS mlz 167 ([M]j. 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, 28466-26-4, other downstream synthetic routes, hurry up and to see.

Adding some certain compound to certain chemical reactions, such as: 1125-29-7, name is 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid, 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 1125-29-7. 1125-29-7

General procedure: To a solution of (S)-2,7-dimethyl-3-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine (15 mg, 53.3 mumol) (Intermediate 40) in CH2Cl2 (0.48 mL) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (prepared according to methods described in Pat. Pub. No. WO2012145581, Oct. 26, 2012) (12.2 mg, 58.7 mumol), HATU (26.4 mg, 69.3 mumol), and N,N-diisopropylethylamine (27.6 muL, 0.16 mmol). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and purified by preparative HPLC (XBridge C18 column (5 mum, 100*4.6 mm), mobile phase of 5-95% ACN in 20 mM aqueous NH4OH) to afford the title compound as a white powder (21 mg, 84% yield). MS (ESI): mass calcd. for C23H18F4N6O, 470.1; m/z found, 471.2 [M+H]+. 1H NMR (600 MHz, DMSO-d6) delta 8.19-8.05 (m, 1.62H), 7.93-7.90 (m, 0.40H), 7.87-7.83 (m, 0.91H), 7.74-7.66 (m, 1H), 7.59-7.38 (m, 3H), 5.59-5.49 (m, 0.74H), 4.73-4.62 (m, 0.28H), 4.57-4.51 (m, 0.17H), 3.81 (s, 2.26H), 3.76 (s, 0.22H), 3.70 (s, 0.52H), 3.64-3.52 (m, 0.72H), 3.38-3.17 (m, 0.73H), 3.07-3.00 (m, 0.22H), 2.84-2.76 (m, 0.15H), 2.71-2.60 (m, 0.63H), 2.45-2.22 (m, 1.47H), 1.47 (d, J=6.7 Hz, 2.28H), 1.35 (d, J=6.8 Hz, 0.6H).

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 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid.

82560-12-1, Name is 3-Amino-5-tert-butylpyrazole, 82560-12-1, 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.

3-(tert-butyl)-lH-pyrazole-5-amine (1.00 g, 7.18 mmol), 3-bromo-5- hydroxypyridine (1.14 g, 6.53 mmol), copper (I) iodide (62.0 mg, 0.33 mmol), K2CO3 (1.90 g, 13.7 mmol) and trans-N, N’-dimethylcyclohexane- l ,2-diamine (186 mg, 1.31 mmol), were weighed in a 20 mL microwave vial fitted with a stirrer bar and sealed with a crimped septum. The vial was then evacuated and purged with N2, and anhydrous toluene (10 mL) added. The resulting mixture vacuum degassed and purged with N2, and then heated at 100C for 24 h. The resulting dark suspension was diluted with EtOAc and filtered through Celite, washed with EtOAc and the filtrates concentrated in vacuo. The resulting residue was purified by FCC, eluting with 0-8% MeOH/DCM, to afford the title compound (1.15 g, 76%). LCMS (Method 3): t 2.31 min, m/z 233.2 [MH+]. NMR (300 MHz, CDC13): 1.32 (9H, s), 3.49 (1H, s), 5.55 (1H, s), 7.37 (1H, t, J = 2.3 Hz), 8.04 (1H, d, J = 2.5 Hz), 8.27 (1H, d, J = 2.1 Hz).

Statistics shows that 3-Amino-5-tert-butylpyrazole is playing an increasingly important role. we look forward to future research findings about 82560-12-1.

10010-93-2, 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. 10010-93-2 name is 3-Methyl-5-(trifluoromethyl)-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.

a) A mixture of potassium carbonate (924 mg, 6.69 mmol), 2-methyl-5-(trifluoromethyl)-1H-pyrazole (501 mg, 3.34 mmol) and methyl 2-bromobutyrate (0.42 mL, 3.7 mmol) in dimethylformamide:tetrahydrofuran (3 mL:6 mL) was heated at 60 C. for 5 h with stirring. After cooling to room temperature, most of tetrahydrofuran was removed by gently blowing nitrogen over the reaction mixture. Ethyl acetate and water were added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 12-17% ethyl acetate in hexanes) to afford the desired product (704 mg, 2.81 mmol, 84%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.