Tag: M.W:100-200

These common heterocyclic compound, 2458-26-6, name is 3-Phenyl-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. COA of Formula: C9H8N2

General procedure: NaH (4.3mg, 0.18mmol) was added to a solution of 15 (42mg, 0.09mmol) and 3-phenyl-pyrazol (38.9mg, 0.27mmol) in DMF (1mL). The solution was heated at 130C for 30min using microwave heating. The reaction was quenched with saturated NaHCO3 (10mL) and EtOAc (15mL) was added. The phases were separated and the organic phase extracted with NaHCO3 (10mL) and concentrated. Yield: 60mg of the crude intermediate (2R,4aR,10aR)-9-methoxy-2-(3-phenyl-pyrazol-1-ylmethyl)-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine.

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

Reference:
Article; Risgaard, Rune; Jensen, Martin; J°rgensen, Morten; Bang-Andersen, Benny; Christoffersen, Claus T.; Jensen, Klaus G.; Kristensen, Jesper L.; Pueschl, Ask; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 381 – 392;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2644-93-1, 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. 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

n-BuLi (2.1 mL, 2.5 M in hexanes, 5.2 mmol) was added drop-wise to a -50 C. solution consisting of 3-(benzyloxy)-6-bromo-4-chloro-2-methoxyquinoline (2.0 g, 5.3 mmol, Intermediate 29: step d) and THF (50 mL). The resultant reaction mixture was stirred at -50 C. for 20 minutes and then treated with a solution of 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (730 mg, 5.28 mmol) and THF (15 mL) at -50 C. The resulting mixture was stirred at room temperature for 20 minutes before quenching with saturated aqueous NH4Cl (20 mL) and extracting with dichloromethane:methanol (5:1, 50 mL*10). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the crude product, which was purified by FCC (silica gel, eluent: petroleum ether:ethyl acetate=5:1 to 1:1) to afford the title compound.

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, 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H8N2O2

NaH (80% in oil, 130 mg, 4.3 mmol, 1 .5 eq.) was added to 4-ethoxycarbonyl-1 H-pyrazole (400 mg, 2.86 mmol, 1 eq.) in THF (8 ml_), and the mixture stirred at r.t. for 30 min. SEMCI (556 muIota_, 3.14 mmol, 1 .1 eq.) was added and the reaction stirred at r.t. for 18 h. The mixture was partitioned between EtOAc (2 x 30 ml_) and water (20 ml_), the organic layers dried (MgS04) and the solvent removed in vacuo. The residue was purified by MPLC on silica with gradient elution from 5-20% EtOAc/petrol to give the title compound as a clear oil (657 mg, 85%); HRMS found 271 .1468 MH+

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 151049-87-5, name is 3-Bromo-1-methyl-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 151049-87-5, Recommanded Product: 151049-87-5

Preparation 45 (1126) -methoxy-4-(1 -methyl-1 -/-pyrazol-3-yl)aniline (1127) (1128) To a solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (310 mg, 1 .244 mmol) and 3-bromo-1 -methyl-1 -/-pyrazole (154 mg, 0.957 mmol) in THF (3 ml_) was added Pd(dppf)Cl2-DCM (40 mg, 0.049 mmol) and 2M aqueous Na2CC>3 (1 ml_) and the reaction was heated to 65 C for 18 hours. The reaction was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, the combined organic layers were washed with water and brine, dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-60% EtOAc in cyclohexane to afford the title compound (34 mg, 18%). (1129) 1 H NMR (500 MHz, CDCI3): delta ppm 7.33 (d, J = 18.8 Hz, 2H), 7.28 (d, J = 1 .2 Hz, 2H), 7.20 (d, J = 7.9 Hz, 1 H), 6.74 (dd, J = 7.9, 1 .2 Hz, 1 H), 6.45 (dd, J = 2.2, 1 .2 Hz, 1 H), 3.95 (m, 6H), 3.85 (br s, 2H). (1130) HRMS (ESI) MS m/z calcd for C11 H14N3O [M+H]+ 204.1 131 , found 204.1 141 .

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:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WOODWARD, Hannah; INNOCENTI, Paolo; NAUD, Sebastien; BLAGG, Julian; HOELDER, Swen; WO2015/128676; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2458-26-6, 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. 2458-26-6 name is 3-Phenyl-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 3-phenyl-1H-pyrazole (188mg, 1.3mmol) in DMF (8mL) was added NaH (60% in oil, 60mg, 1.5mmol) and the solution was stirred for 5min. To the solution was added compound 78a (200mg, 1.Ommol) and the solution was heated to 6O0C for 1h. Allowed to cool, concentrated under vacuum, and purified by preparative TLC (30%EtOAc/hexanes) to yield compound 78b(61 mg, 20%).

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

Reference:
Patent; SCHERING CORPORATION; WO2009/111442; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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 1 In a flask were combined 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), cyclopropylboronic acid (886 mg, 10.3 mmol) and sodium carbonate (1.09 g, 10.3 mmol) and the mixture suspended in 1,2-dichloroethane (20 mL). A suspension of copper (II) acetate (936 mg, 5.16 mmol) and 2,2-bipyridine (805 mg, 5.16 mmol) in 1,2-dichloroethane (40 mL) was warmed to 50 C. and added and the resulting mixture heated at 70 C. overnight. The mixture was then cooled and filtered and the solids rinsed with EtOAc. The combined filtrates were concentrated and the residue taken up in EtOAc and 50% saturated aqueous NH4Cl. The organic layer was washed with sat NH4Cl, sat NaHCO3 and sat NaCl and dried over MgSO4. The solution was concentrated and the residue purified by SiO2 chromatography (5-35% EtOAc/heptane) to afford 517 mg (43%) 1-cyclopropyl-4-iodo-1H-pyrazole as a colorless oil.

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); 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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Quality Control of 1-Methyl-4-nitro-1H-pyrazole

Example 1 5-chloro-1-methyl-4-nitro-1H-pyrazole [0177] 4-nitro-1-H-pyrazole (5 g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CH2Cl2 (2×150 mL). The organic layer was separated and the solvent was distilled off to yield 1-methyl-4-nitro-1H-pyrazole as a white solid (4.30 g, 76%). [0179] Following WO 2007/99326, to a 500 mL 3-neck-round bottom flask was added 1-methyl-4-nitro-1H-pyrazole (4.30 g, 33.8 mmol) and THF (12 mL). The mixture was cooled to -78 C. and lithium hexamethyldisilazide in THF (1M, 88.4 mL, 90 mmol) was added dropwise via an addition funnel over 20 min. The brown mixture was stirred for 30 min and warmed to -45 C. over 30 min. The mixture was cooled back down to -78 C. and hexachloroethane (10.5 g, 44.2 mmol) dissolved in THF (20 mL) was added via an addition funnel over 15 min. The mixture was stirred for 2.5 h, warmed from -78 C. to -40 C. and the reaction was monitored by LCMS. Upon completion of the reaction, the reaction was quenched with a solution of saturated NH4Cl (150 mL), and ethyl acetate (100 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (150 mL), dried over Na2SO4 and the organic solvent was distilled off. The crude product was purified via flash chromatography (CH2Cl2/7% MeOH) to yield 5-chloro-1-methyl-4-nitro-1H-pyrazole as a white solid (1.40 g, 20%). 1H NMR (400 MHz, CDCl3) delta 8.13 (s, 1H), 3.92 (s, 3H); ESIMS m/z=162.0 (M+1)

The synthetic route of 3994-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 309740-49-6, A common heterocyclic compound, 309740-49-6, name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, molecular formula is C6H7N3O4, 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.

B) Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate To a solution of methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (8.62 g) in methanol (100 mL), palladium-carbon (10%) (0.86 g) was added, and the mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere (40 psi). Palladium-carbon was filtered off, and then, the filtrate was concentrated to obtain the title compound (4.71 g). 1H NMR (400 MHz, CDCl3) delta 3.91 (3H, s), 4.03 (3H, s), 4.15 (2H, brs), 7.07 (1H, s).

The synthetic route of 309740-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (2018); 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. 1780-72-9, name is 4-Bromo-5-methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Computed Properties of C4H6BrN3

General procedure: Kinetics of reactions were followed using stopped-flow technique by measuring the change in absorbance as a function of time at suitable wavelengths. The working wavelengths were determined by comparing consecutive spectra of the reaction mixture over the wavelength range 200-600 nm. The reactions were studied under the pseudo-first-order conditions, which means that the concentration of entering ligand was always much higher (at least a 10-fold times) than the concentration of complex ([complex]e = 1 * 10-4 M, [ligand]e = from1 * 10-3 M to 5 * 10-3 M). Reactions were initiated in the stopped-flow instrument by mixing equal volumes of complex solution and entering ligand solution. Reactions were followed for at least eight half-lives. Kinetic traces were fitted as a double-exponential function. The pseudo-first-order rate constants, kobsd1 and kobsd2,were obtained as average values from four to eight independent kinetic runs. All reactions were studied at three different temperatures (from 15 to 35 C) to determine the activation parameters.

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; Kosovi?, Milica; Ja?imovi?, ?eljko; Bugar?i?, ?ivadin D.; Petrovi?, Biljana V.; Transition Metal Chemistry; vol. 41; 2; (2016); p. 161 – 168;,
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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3BrN2

Production Example 60 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-1-yl)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 59”). [Show Image] 1H-NMR (CDCl3) delta: 8.92 (s, 1H), 8.89 (d, J=5.1 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 8.08-8.07 (m, 1H), 7.69 (dd, J=8.8, 1.2 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7. 59 (d, J=8.8 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H)

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

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics