Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 3469-69-0, name is 4-Iodopyrazole, 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 3469-69-0, Application In Synthesis of 4-Iodopyrazole

General procedure: To a solution of pyrazole 1-13 (1 equiv.) and trifluoroacetic acid (0.01 equiv.) in dichloromethane(for 1 mol of pyrazole – 1 L of dichloromethane were used) ethyl vinyl ether (1.27 equiv.) wasadded dropwise, keeping the temperature between 28-32 C (exothermic reaction) and left to stir atroom temperature for 12-78 hours. Dichloromethane was washed with saturated NaHCO3 solution(1 × 250 mL – for 1 L of dichloromethane) then with deionized H2O (1 × 250 mL). Organic layerwas dried with anhydrous Na2SO4, and evaporated under reduced pressure. Products were purifiedby distillation or recrystallization.

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, 4-Iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mazeikaite, Rita; Sudzius, Jurgis; Urbelis, Gintaras; Labanauskas, Linas; ARKIVOC; vol. 2014; 6; (2014); p. 54 – 71;,
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. 49633-25-2, name is 3-Isopropylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Isopropylpyrazole

Part A – 4-Bromo-3-isopropylpyrazole To a stirred solution of sodium acetate (19.7 g., 0.24 mole) in acetic acid (100 ml.) and water (15 ml.), 3-isopropylpyrazole (11.0 g., 0.1 mole) was added, followed by dropwise addition of bromine (16.0 g., 0.11 mole) keeping the internal temperature below 15 C. The mixture was kept at 25 C. for 15 hours, treated with water (200 ml.) and extracted with ethyl ether (3 * 50 ml.), and the ether layer washed with water (1 * 50 ml.) dried, (sodium sulfate) and evaporated under reduced pressure. The resultant pale yellow oil was distilled to give 4-bromo-3-isopropylpyrazole (15.3 g., 81%) with a boiling point of 85 C. at 0.06 mm Hg. Analysis: Calc’d. for C6 H9 BrN2: C, 38.11; H, 4.80; N, 14.82; Br, 42.27. Found: C, 37.91; H, 4.89; N, 14.83; Br, 42.15.

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; The Upjohn Company; US3957480; (1976); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-12-0,Some common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H8N2O, 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: To a solution of Example 13 (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, A new synthetic method of this compound is introduced below., name: 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: A mixture of 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 1a (1.0 mmol), Ketones 2(1.0 mmol) and InCl3 (10 mol%,) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table 3. After completion of the reaction (indicated by TLC) the reaction mixture was filtered and wash with acetonitrile (2 X 5 mL) to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated with MTBE (10 mL), filtered and dried to give the desired product.

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; Ismail; Kuthati, Bhaskar; Thalari, Gangadhar; Bommarapu, Venkatesham; Mulakayala, Chaitanya; Chitta, Suresh Kumar; Mulakayala, Naveen; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1446 – 1450;,
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. 7119-95-1, name is 1-Nitropyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A solution of 1-nitro-1H-pyrazole (4.00 g, 35.4 mmol) in 40 mL of benzonitrile was refluxed for 2 h. After being cooled to 25° C., the mixture was poured into 160 mL of hexanes. A white solid precipitated which was filtered and dried in vacuo, to afford 3-nitro-1H-pyrazole (3.16 g, 79percent). H1-NMR (400 MHz, DMSO-d6) delta: 7.01 (1H, d, J=2.4 Hz), 8.01 (d, 1H, J=3.4 Hz).

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; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (2008); 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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C4H8ClN3

The 2,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine (430mg, 1.4046 mmol), diisopropylethylamine (546.7 mg, 4.23 mmol) and 1-methylpyrazol-4-amine hydrochloride (283.3 mg,2.12 mmol) was dissolved in n-BuOH (10 mL), the temperature of the reaction solution was raised to 150 C, sealed tube reaction for 23 hours, and then concentrated under reduced pressure.The residue was purified by silica gel column chromatography (DCM / MeOH (v / v) = 50/1) to afford the title compound as a white solid which was recrystallized from acetone to give the title compound as a white solid (220 mg, 42.6% ).

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Li Xiaobo; Dai Weilong; Wang Tingjin; (74 pag.)CN104926824; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 52222-73-8, 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. 52222-73-8 name is 4-(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.

(5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-(trifluoromethyl)- lH-pyrazol- l-vDpropanamide C16H12F6N (0773) (0774) [00351] To a solution of 4-trifluoromethyl-pyrazole (0.20 g, 0.00147 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.18 g, 0.004409 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8) (0.516 g, 0.00147 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and ethyl acetate (19: 1) as eluent to afford 0.30 g (50%) of the titled compound as white foam. (0775) [00352] Compound 1017 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.38 (s, 1H, NH), 8.45 (d, = 2.0 Hz, 1H, ArH), 8.25-8.22 (m, 2H, ArH & Pyrazole-H), 8.11 (d, = 8.2 Hz, 1H, ArH), 7.82 (s, 1H, Pyrazole-H), 6.39 (s, 1H, OH), 4.55 (d, = 14.0 Hz, 1H, CH), 4.37 (d, = 14.0 Hz, 1H, CH), 1.40 (s, 3H, CH3); Mass (ESI, Positive): 407.0945 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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 176969-34-9, SDS of cas: 176969-34-9

N dichloromethane 1ml solution of 3-difluoromethyl-1-methyl -1H- pyrazole-4-carboxylic acid 176mg, added N- dimethylformamide 10mg and oxalyl chloride 381mg, I was stirred at room temperature for 1 hour.After completion of the reaction, distilling off the solvent under reduced pressure, the residue was dissolved in dichloromethane 2ml, 2- amino-1- (3,5-dichloropyridine prepared with stirring under ice-cooling, at step 5 Synthesis Example 2 2-yl) ethanone -O- dichloromethane 2ml solution of ethyl oxime 190mg, then dropped the pyridine 91mg, was continued for a further 2 hours stirring at room temperature after completion of the dropping.After completion of the reaction, and extracted with added water 10ml reaction mixture chloroform (20mlx1), after the organic layer washed with water (10mlx1), and dehydrated and dried in this order brine then anhydrous sodium sulfate, and distilling off the solvent under reduced pressure It was.The residue was ethyl acetate – hexane (1: 4 to 1: 1 gradient) was purified by silica gel column chromatography eluting with, to give a pale yellow resinous substance 165.3mg.The thing is dissolved in acetic acid 5ml, After stirring for 2 hours at 70 , distilling off the solvent under reduced pressure, the residue partitioned between ethyl acetate – hexane (1: 4 to 1: 1 gradient) and eluting with It was purified by silica gel column chromatography, and the desired compound 130.6mg obtained as a colorless resin-like substance (E / Z = 1/1).

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, 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; Iwasa, Motoyoshi; Tomizawa, Mitsutaka; Tsuji, Keisuke; Nakamura, Toshiyuki; Mita, Takeshi; Kuwahara, Hidehito; asahi, Miho; Imanaka, Hotaka; (342 pag.)JP2016/11286; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-8-carboxylate (294 mg, 0.94 mmol, 1 eq), cesium carbonate (918 mg, 2.82 mmol, 3 eq), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (271 mg, 1.41 mmol, 1.5 eq) and Pd(dppf)Cl2DCM (103 mg, 0.14 mmol, 0.15 eq) were combined in a vial which was sealed and placed under an inert atmosphere. A 1,4-dioxane/H2O solution (4 mL, 5:1 ratio, degassed) was then added via syringe. The resulting mixture was heated to 90 C. overnight, after which time the reaction was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure. The crude residue was purified by RP-HPLC (10-40% MeCN in 0.1% TFA aqueous solution over 20 min), and fractions containing product were basified with sat. NaHCO3, and extracted with 3:1 chloroform/IPA. Combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound as a slightly brown oil (159 mg, 49% over 2 steps). 1H-NMR (400 MHz, CDCl3) delta 9.13 (s, 1H), 8.18 (d, J=8.1 Hz, 1H), 7.98 (s, 1H), 7.91 (d, J=2.3 Hz, 1H), 7.76-7.71 (m, 2H), 7.68-7.64 (m, 2H), 7.54-7.47 (m, 1H), 7.31 (d, J=8.4 Hz, 2H), 6.46 (t, J=2.0 Hz, 1H), 4.23 (s, 2H), 4.06 (s, 3H). ES-MS [M+H]+=344.4.

The synthetic route of 1-(4-(Chloromethyl)phenyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Bender, Aaron M.; US2020/131159; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 13808-62-3 as follows. Recommanded Product: 13808-62-3

EXAMPLE 126 alpha-Bromo-N,N,4-trimethyl-3-phenylpyrazole-1-propionamide Following the procedure of Example 121, but substituting 2,3-dibromo-N,N-dimethylpropionamide for 2-bromo-N,N,2-trimethylpropionamide and 4-methyl-3-phenylpyrazole for 3-phenylpyrazole there was obtained alpha-bromo-N,N,4-trimethyl-3-phenylpyrazole-1-propionamide having a melting point of 104-107 C. Analysis: Calc’d. for C15 H18 BrN3 O: C, 53.58; H, 5.39; N, 12.50; Br, 23.77. Found: C, 53.99; H, 5.51; N, 12.63; Br, 23.43.

According to the analysis of related databases, 13808-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Upjohn Company; US4072498; (1978); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics