Day: August 18, 2021

Electric Literature of 31108-57-3,Some common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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: The appropriate carboxylic acid (1.0 equiv) was treated with oxalyl chloridie (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture was stirred at room temperature for 1 h. The solvent was removed under N2 and the acid chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2 and cooled to 0 C. The acid chloride was added dropwise and the reaction mixture was stirred at room temperature for 3 h. The mixture was diluted withEtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude product that was purified by flash chromatography(SiO2).

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H10N2

Alternative Synthesis for N,N,alpha,4-tetramethyl-3-phenylpyrazole-1-acetamide A mixture of 4-methyl-3-phenylpyrazole (3.65 g., 0.023 mole) N,N-dimethyl-2-chloropropionamide (3.78 g., 0.027 mole) and anhydrous potassium carbonate (4.4 g., 0.032 mole) was heated with stirring at 130 C. for 6 hours. The reaction mixture was cooled and crystallized from 50% aqueous methanol to give 4.5 g. of N,N,alpha,4-tetramethyl-3-phenylpyrazole-1-acetamide as large rods, m.p. 87-89 C.

The synthetic route of 13808-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Upjohn Company; US4072498; (1978); A;,
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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O2

Preparation of Compound 77 Compound 75 was prepared according to J. Heterocycl. Chem., 2003, 487. Compound 75 (10 g, 71.4 mmol), compound 76 (20 g, 89.2 mmol) and K2CO3 (12.328 g, 89.2 mmol) were dissolved in NMP (60 ml), and the mixture was heated to 80° C. for 2 h. The reaction mixture was allowed to cool and diluted with a mixture of ethyl acetate: water=3:1 (500 ml). The water layer was washed with EtOAc (3.x.100 ml), and the organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified on silica gel (PE:EA=100:1 to 20:1) to give compound 77 as yellow oil (2.2 g, 10.9percent). 1H NMR (400 MHz, CDCl3): 0.860 (q, 6H, J=4 Hz), 0.978 (m, 1H), 1.213 (m, 1H), 1.372 (t, 3H, J=7.2 Hz), 1.555 (m, 2H), 2.329 (m, 2H), 3.709 (s, 3H), 4.334 (q, 2H, J=7.2 Hz), 5.907 (q, 1H, J=5.2 Hz), 6.896 (d, 1H, J=2 Hz), 7.587 (d, 1H, J=2 Hz). MS-ESI: m/z=283.1 [M+1]+.

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; INTERMUNE, INC.; US2009/257979; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 71229-85-1, 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. 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 6-chloro-7-fluoro-1H-indole 8 (400 mg, 2.36 mmol) in toluene (10 mL) were added 4-bromo-1-ethyl-1H-pyrazole 4 (Step 3 above; 414 mg, 2.36 mmol), potassium phosphate (1.25 g, 5.91 mmol), N,N’-dimethylethylenediamine (84 mg, 0.95 mmol) and Cu(I)I (45 mg, 0.24 mmol) at RT under inert atmosphere. The resulted solution was purged with argon and sealed the tube. The reaction mixture was then heated to 140 C. for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT, diluted with hexane (10 mL) and filtered through a short pad of celite. The filtrate was washed with water (2*10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified (silica gel chromatography; 8-10% EtOAc/Hexanes) to afford compound 9 (224 mg, 36%) as a light brown thick liquid. 1H NMR (500 MHz, CDCl3): delta 7.64 (s, 1H), 7.61 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.12-7.07 (m, 2H), 6.60-6.59 (m, 1H), 4.22 (q, J=7.5 Hz, 2H), 1.55 (t, J=7.5 Hz, 3H); LC-MS (ESI): 94.7%; m/z 264.1 (M+H+); (column: X Select C-18, 50*3.0 mm, 3.5 mum); RT 3.87 min; 5 mM NH4OAc: ACN; 0.8 mL/min).

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

Reference:
Patent; PHARMAKEA, INC.; Evans, Jillian Frances; US9051320; (2015); B1;,
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. 4522-35-4, name is 3-Iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H3IN2

To a mixture of 180 (193.97mg, i.OOrnrnol) and 28 (139.10mg, i.OOrnmol) in DMF (5rnL), was added C52CO3 (325.82mg, 1 .OOmmol) in one portion at room temperature. The mixture was then heated to 80uC for 1 5 hours under N2 atmosphere. ILC showed the reaction was completed. Themixture was cooled to room temperature and was then poured into water (i5mL) slowly. A white solid precipitated out from the mixture, filtered off. The solid was dried to afford product 197 (300.00 mg, yield: 67.08%).LCMS: m/, 313.9 (M±H.

According to the analysis of related databases, 4522-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 154471-65-5, 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 154471-65-5 as follows.

Preparation 7[1 -Methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yllboronic acidTo a stirred solution of 1 -methyl-3-(thfluoronnethyl)-1 H-pyrazole (1 .89 g, 12.6 mmol) in anhydrous tetrahydrofuran (20 ml_) under nitrogen cooled to -78C was added n- butyllithium (8.3 mL, 1 .6 M solution in hexanes, 13.2 mmol) slowly over 5 minutes. The resulting yellow solution was stirred at -78C for 1 hour and trimethyl borate (1 .56 mL, 13.9 mmol) was then added slowly. The reaction flask was covered in foil and allowed to warm to room temperature for 16 hours. The white solution was quenched with aqueous 1 M hydrogen chloride solution (10 mL) and stirred at room temperature for 1 .5 hours. The mixture was extracted with ethyl acetate (2 x 30 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo to give an off-white foam (2.1 1 g). The foam was triturated with dichloromethane, filtered and dried in vacuo to afford the title compound as a white solid (1 .57 g, 64%).1H NMR (400 MHz, MeOH-d4): delta 4.04 (s, 3H), 6.89 (s, 1 H).LCMS Rt = 1 .1 1 minutes MS m/z 194 [MH]+ 192 [M-H]-,

According to the analysis of related databases, 154471-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan, Daniel; RAWSON, David, James; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2012/7868; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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.

To a solution of2,4-difluoro-l-nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in THF (20 ml) was added dropwise the solution of 5-cyclopropyl-1H-pyrazol-3- amine (0.91 g, 7.39 mmol) in THF (5 ml) at 25 C. After addition, the reaction mixture was stirred at 80 C for 48 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : DCM : EtOAc = 2 : 1 : 1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, 1H), 9.83 (s, 1H), 8.25 (m, 1H), 7.98 (d, J= 11.2 Hz, 1H), 6.75 (m, 1H), 5.95 (s, 1H), 1.90 (m, 1H), 0.96 (m, 2H), 0.72 (m, 2H).

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
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. 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methyl-1-phenyl-1H-pyrazole

General procedure: In a typical experiment,the aryl bromide (3 mmol), heteroaromatic 1, 21 or 23 (1 mmol), KOAc(0.588 g, 6 mmol) and PdCl(C3H5)(dppb)16 (0.012 g, 0.02 mmol) were dissolvedin DMA (4 mL) under an argon atmosphere. The reaction mixture was stirred at 150 C for 72 h. Then, the solvent was evaporated and the product was purified by silica gel column chromatography.

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:
Article; Takfaoui, Abdelilah; Zhao, Liqin; Touzani, Rachid; Dixneuf, Pierre H.; Doucet, Henri; Tetrahedron Letters; vol. 55; 10; (2014); p. 1697 – 1701;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-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 13599-12-7, category: pyrazoles-derivatives

General procedure: A mixture of ethyl 3-aryl-1H-pyrazole-5-carboxylate 1 (2 mmol), N-aralkyl -2-chloroacetamide 7 (3 mmol), anhydrous potassium carbonate (4 mmol) and dry acetonitrile (60 ml) was refluxed for 1-5 h, after which the mixture was cooled to room temperature and filtered. The filtrate was condensed under reduced pressure. The crude product was purified by chromatographer on silica gel using PE/EtOAc (3:1) as an eluent to afford the desired compounds 5.

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.

Reference:
Article; Lv, Hong-Shui; Kong, Xiang-Qian; Ming, Qian-Qian; Jin, Xing; Miao, Jun-Ying; Zhao, Bao-Xiang; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 844 – 849;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Example 113; 4-(3,5-Difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (113b) (0.308 g, 0.00096 mol), EDCI (0.28 g, 0.0015 mol), HOBt (0.21 g, 0.0015 mol) and NMM (0.49 g, 0.0048 mol) in CH2Cl2 (15 mL) was added 1-methyl-1H-pyrazol-3-amine (0.11 g, 0.001 mol) in one portion. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aq. citric acid and then sat. NaHCO3. The organic phase was dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by prep. HPLC to give the title compound (95 mg, 51percent yield) as a white solid. 1H NMR (400 MHz, CDCl3): delta 8.82 (s, 1H), 7.20 (m, 2H), 7.03 (d, 2H), 6.73 (s, 1H), 6.42 (m, 3H), 3.72 (s, 3H), 2.84 (s, 2H), 1.42 (s, 6H); LCMS for C21H19F2N3O3 m/z 400.4 (M+H)+.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2008/280875; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics