Day: July 9, 2021

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

Some common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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: 120068-79-3

General procedure: Phenylpyrazole (0.2 mmol), arylboronic acid (0.4 mmol), NIS (0.2 mmol), [Pd] (10 mol%), NaHCO3 (0.4 mmol) and C2H5OH:H2O (3:1, 10 mL), were added to a Schlenk tube. Then the tube was charged with N2 and the reaction mixture was stirred at 80 C for 18 h. After the completion of the reaction, as monitored by TLC, the mixture was cooled and filtrated. The filtrate was extracted with ethyl acetate and washed with brine. Then the combined organic extracts were dried over Na2SO4, concentrated under vacuum and the resulting residue was purified by silica gel column chromatography to afford the desired products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 120068-79-3, its application will become more common.

Reference:
Article; Lv, Ting; Zhang, Xiao-Hong; Han, Jiang-Sheng; Zhong, Ping; Journal of Fluorine Chemistry; vol. 137; (2012); p. 44 – 49;,
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

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

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

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., Recommanded Product: 3-Iodo-1H-pyrazole

A mixture of 3-iodo-1H-pyrazole (5 g, 25.78 mmol), 3,4-dihydro-2H-pyran (10 g, 118.88 mmol), p-TsOH (900 mg, 5.23 mmol) in tetrahydrofuran (100 mL) was refluxed overnight. The reaction mixture was cooled to room temperature and washed with sat. NaHCO3 (20 mL). The organic layer was separated, dried over Na2SO4, filtered and evaporated. The residue was purified with silica-gel column chromatography (PE:EA=20:1 to 10:1) to give 3-iodo-1-tetrahydropyran-2-yl-pyrazole (7 g, 98% yield) as a light yellow oil. LCMS (ESI) [M+Na]+=300.9. 1H NMR (400 MHz, CDCl3) delta 7.45 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 5.39-5.36 (m, 1H), 4.08-4.04 (m, 1H), 3.72-3.66 (m, 1H), 2.10-2.01 (m, 2H), 1.73-1.54 (m, 4H).

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; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, 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.

Under anhydrous condition, to a solution of ethyl 4-pyrazolecarboxylate (600 mg) in DMF (21ml, c=0.1 molL-1) cooled by an ice bath, NaH (in mineral oil 60%, 225 mg, 1.3 equiv.) was added in 3 portions (over 5 minutes). The mixture was stirred for 15 minutes, then methyl iodide (410 muL, 1.2 equiv.) was added. The ice bath was removed and the reaction was stirred at room temperature for 1 Hrs. The mixture was hydrolysed with a saturated aqueous solution of NaHCO3 (200 ml) and extracted twice with EtOAc (2*250 ml). The organic layers were combined, washed with brine (400 ml), dried over MgSO4 and concentrated. Purification by flash-chromatography (AcOEt in cyclohexane, 5 to 100%) afforded compound 107 as a colourless oil in 90% yield. 1H-NMR (400 MHz, DMSO): 1.26 (t, J 7.1 Hz, 3H, O-CHrCH3); 1.38 (t, J 7.3 Hz, 3H, N-CHrCH3); 4.17 (q, J 7.3 Hz, 2H, N-CH2-CH3); 4.21 (q, J 7.1 Hz, 2H, O-CH2-CH3); 7.84 (s, 1H, Ar);8.33 (s, 1H, Ar). M/Z (M+H)+ = 169.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-pyrazolecarboxylate, its application will become more common.

Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 59340-27-1, 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 59340-27-1 as follows.

2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-l-one acetic acid salt (0.02 g, 0.05 mmol) was dissolved in pyridine (0.5 ml) at room temperature and 1,3,5-trimethyl- lH-pyrazole-4-sulfonyl chloride (0.013 g, 0.06 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in AcOEt and washed with 0. IM HCl and brine. The organic layer was dried (Na2SO4), filtered and evaporated under reduced pressure to give a crude residue which was purified by flash column chromatography (4:1 AcOEt/heptane) to yield 2-(4-trifluoromethoxy-phenyl)-8-(l,3,5-trimethyl-lH-pyrazole- 4-sulfonyl)-2,8-diaza-spiro[4.5]decan-l-onel)-2,8-diaza-spiro[4.5]decan-l-one as an off- white solid (0.09g, 31%). MS (ESI): 487.3(MH+)

According to the analysis of related databases, 59340-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ACKERMANN, Jean; CONTE, Aurelia; HUNZIKER, Daniel; NEIDHART, Werner; NETTEKOVEN, Matthias; SCHULZ-GASCH, Tanja; WERTHEIMER, Stanley; WO2010/130665; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37622-90-5, 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. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, 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.

292.1 (1H-pyrazol-4-yl)-methanol To a suspension of LiAlH4 (5.3 g) in dry THF (100 mL) in a round-bottomed flask, under inert atmosphere (N2), was added portionwise ethyl pyrazole-4-carboxylate (10.0 g) at rt. The reaction mixture was stirred at rt overnight and then poured into a sat. aq. Rochelle salt solution. The mixture was stirred at rt for 3 h and diluted with EA. The layers were separated and the aq. layer was extracted with EA (3*). The combined org. layers were dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, after drying, as a white solid (5.2 g; 76% yield). 1H NMR (d6-DMSO) delta: 12.60 (s, 1H); 7.50 (s, 2H); 4.77 (br. s, 1H); 4.38 (br. s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Methyl-1H-pyrazol-3-amine

General procedure: Amino-pyr azole 1 (0.291 g, 0.003 mol) and an aqueous solution of NaBr (100 mL) (concentrations were as follows: 1 in entries 1 and 2, 2 Min entries 3 and 5-9, and 3 in entry 4) were placed in a cell. In experiment 2, NaHCO3 (0.504 g, 0.006 mol) was added to the solution. The electrolysis was carried out at the following currents: 426 mA for entries 1-4, 213 mA for entry 5, 710 mA for entries 6, 8, and 9, and 852 mA for entry 7. In experiment 9, 48% aqueous solution of HBr was periodically added to the reaction mixture to maintain 7. After passing 2 F of electricity per 1 mole of the starting aminopyrazole 1(Q= 579 C) for entries 1-7or 8 F (Q= 2316 C) for entries 8and 9, the electrolysis was stopped, the reaction mixture was stirred for 1 h and analyzed by TLC (eluent light petroleum ether-ethyl acetate (1 : 1)). Then, the mixture obtained was diluted with concentrated HCl (to 3) and the products were extracted with CHCl3 (3×30 mL). The extracts were combined, dried with anhydrous MgSO4, and concentrated in vacuo. The products were isolated using column chromatography on SiO2 (eluent light petroleum ether-ethyl acetate). The following compounds were isolated: 1,2-bis(1-methyl-1H-pyrazol-3-yl)-diazene (7) (entries 1-7; the product was identified by m.p. 201-202 C (cf. Refs 2 and 4: m.p. 201 C) and the reported 2,41 NMR spectra) and 1,2-bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8) (entries 8 and 9, the product was identified by NMR spectroscopy and high resolution mass spectrometry). The aqueous layer obtained after extraction was concentrated in vacuo, diluted with NaOH with stirring (to 10), and treated as described above. This resulted in the isolation of 3-amino-4-bromo-1-methyl-1H-pyrazole (6) (entries 1-9; the product was identifi ed by m.p. 97 C (cf. Ref. 10: m.p. 97-98 C) and the reported 51 NMR spectra) and unreacted aminopyr-azole 1(entries 1-8; the starting compound was identified by TLC and NMR spectroscopy). 1,2-Bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8).Yellow crystals. M.p. 211-213 C. Rf 0.13 (eluent light petroleum ether-ethyl acetate (1:5)). 1H NMR, :4.02 (s, 6 H, Me); 7.50 (s, 2 H, CH). 13C NMR, :40.4 (2 Me), 90.1 (2 CBr), 132.9 (2 CH), 157.5 (2 CN). Found: m/z 348.9217 [M + H]+. C8H979Br2N6. Calculated: [M + H]+= 348.9230

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 1904-31-0.

Reference:
Article; Lyalin; Sigacheva; Kokorekin; Dutova, T. Ya.; Rodionov; Petrosyan; Russian Chemical Bulletin; vol. 67; 3; (2018); p. 510 – 516; Izv. Akad. Nauk, Ser. Khim.; 3; (2018); p. 510 – 516,7;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics