Category: 39806-90-1

Electric Literature of 39806-90-1, 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 39806-90-1 as follows.

Example 58. Synthesis of (R)-5-(l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6- dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepin-8-yl)pyridin-2-amine (Compound 76). The title compound was synthesized by the following scheme:[00393] (R)-8-bromo-l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepine (Step 1). A mixture of (R)-8-bromo-l,4-dimethyl-5,6- dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (292 mg, 1 mmol), 4-iodo-l-methyl- lH-pyrazole (312 mg, 1.5 mmol), copper (I) iodide (58 mg, 0.3 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium phosphate (424 mg, 2 mmol) in dimethyl sulfoxide (10 mL) was heated at 150C for 14 hours under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (20 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give (R)-8-bromo-l,4-dimethyl- 6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [1,2,4] triazolo[4,3-d][l,4]diazepine which was used in the next step without further purification. LRMS (M+H)+: calcd 372.07; found 372.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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. name: 4-Iodo-1-methyl-1H-pyrazole

To a solution of 4-iodo-1-methyl-pyrazole (2.68 g, 12.9 mmol) and tert- butyl piperazine-1 -carboxylate (2.00 g, 10.7 mmol) in /-PrOH (40 ml_), ethylene glycol (0.66 g, 10.7 mmol), Cul (0.41 g, 2.15 mmol) and K3P04 (9.12 g, 43.0 mmol) were added. The reaction mixture was heated in sealed tube at 100C for 20h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated in vacuo. The residue was diluted with H2O (150 ml_) and extracted with EtOAc (3 * 100 ml_). The organic layer was separated, washed with brine (100 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 0 to 2% MeOH in DCM) to afford tert-butyl 4-(1-methylpyrazol-4- yl)piperazine-1-carboxylate (0.93 g, 33%) as off-white solid. MS (ESI) m/e [M+H]7Rt/%: 267.00/2.45/82.5%. 1H NMR (400 MHz, CDCI3) 51.49 (s, 9H) 2.84 – 2.92 (m, 4H) 3.53 – 3.60 (m, 4H) 3.84 (s, 3H) 6.95 (s, 1 H) 7.21 (s, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39806-90-1, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; HALL, Adrian; (62 pag.)WO2018/138086; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1,Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

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

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

The synthetic route of 4-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-iodo-l-methyl-lH-pyrazole (20.14 mg, 0.097 mmol) in anhydrous DMSO (5 ml) was added intermediate 20.1-2 (20 mg, 0.065 mmol), (iras,)-Nl,N2-dimethylcyclohexane- 1, 2-diamine (1.837 mg, 0.013 mmol), potassium phosphate (41.1 mg, 0.194 mmol) and Cul (1.230 mg, 6.46 pmol). The resulting mixture was stirred at 90C under N2 protection for 12 hours. After filtration and concentration, the crude product was purified by pre-HPLC (TFA) to give example 20.2-2, ( R,R or .V,.Y)-5-chloro-6-(3-nuoro- 1 -(oetan-3-yl)piperidin-4-yl)- 1 -( 1 -methyl- 1 H-pyra/ol- 4-yl)-lH-indazole, TFA salt. MS (ESI) m/z calc?d for C19H22CIFN5O [M+H]+ 390, found 390. NMR (400 MHz, CD3OD) d 8.27 (s, 1H), 8.17 (s, 1H), 7.95 (s, 1H), 7.89 (s, 1H), 7.65-7.85 (m, 1H), 5.39-5.62 (m, 1H), 5.39-5.62 (m, 1H), 4.95-5.05 (m, 4H), 4.59 (m, 1H), 4.02 (s, 3H), 3.81- 4.00 (m, 2H), 3.56 (m, 1H), 3.11-3.26 (m, 2H), 2.20-2.37 (m, 2H). LRRK2 IC50 5.8 nM.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1, These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-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.

To a solution of 4-iodo-1-methyl-1H-pyrazole (3.0 g, 14.4 mmol, 1.0 eq.), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (835 mg, 1.4 mmol, 0.1 eq.) and palladium(II) acetate (415 mg, 0.7 mmol, 0.05 eq.) in dioxane (72.1 ml, 0.2 M) was added N,N’-diisopropylethylamine (5.0 mL, 28.9 mmol, 2.0 eq.) and benzylmercaptan (2.0 ml, 17.3 mmol, 1.2 eq.). The reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with ethyl acetate (300 mL) and water (150 mL). The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography.

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vernier, William F.; Gomez, Laurent; Tetrahedron Letters; vol. 58; 49; (2017); p. 4587 – 4590;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-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. SDS of cas: 39806-90-1

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

The synthetic route of 4-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

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-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2109; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-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 39806-90-1, Recommanded Product: 39806-90-1

A mixture of 2-(3-{3-[5-benzyloxy-2-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (1.00 g, 1.47 mmol), 4-iodo-1-methylpyrazole (450 mg, 2.16 mmol), cesium carbonate (1.20 g, 3.62 mmol), and PdCl2(dppf) (72 mg, 0.088 mmol) in de-oxygenated toluene (35 mL) was heated at 100 C. for 24 h. Additional portions of 4-iodo-1-methylpyrazole (~30 mg) and PdCl2(dppf) (~30 mg) were added and heating continued at 100 C. for 40 h. The mixture was cooled to room temperature, concentrated in vacuo, diluted with methylene chloride, and filtered down a short plug of silica gel. The filtrate was concentrated in vacuo. Chromatography (silica gel, 35% ethyl acetate/65% hexane to 65% ethyl acetate/35% hexane) of the residue provided 710 mg (76%) of the title compound. 1H NMR (CDCl3) delta 7.86 (dd, J=8, 2 Hz, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.37 (m, 6H), 7.28 (s, 1H), 7.09 (d, J=9 Hz, 1H), 7.04 (d, J=9 Hz, 1H), 6.78 (d, J=9 Hz, 1H), 6.67 (d, J=9 Hz, 1H), 6.56 (s, 1H), 6.42 (d, J=8 Hz, 1H), 5.08 (s, 2H), 4.18 (t, J=6 Hz, 2H), 4.15 (t, J=6 Hz, 2H), 3.85 (s, 3H), 3.81 (s, 3H), 2.63 (t, J=8 Hz, 2H), 2.59 (q, J=7 Hz, 2H), 2.30 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=8 Hz, 2H), 1.23 (t, J=7 Hz, 3H), 0.89 (t, J=7 Hz, 3H).

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; Eli Lilly and Company; US6797723; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-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 39806-90-1, Safety of 4-Iodo-1-methyl-1H-pyrazole

tert-butyl 3 ,8-diazabicyclo [3.2.1 ]octane-3-carboxylate (250 mg, 1.18 mmol), 4-iodo- 1-methyl- 1H-pyrazole (0.32 g, 1.5 mmol), sodium 2-methylpropan-2-olate (0.17 g, 1.8 mmol), methanesulfonato(2-dicyclohexylphosphino-2?,6?-di-i-propoxy- 1,1 ?-biphenyl)(2?-amino- 1,1biphenyl-2-yl)palladium(II) (0.10 g, 0.12 mmol) and toluene (4 mL) were charged in a vial. The headspace was flushed with nitrogen and the reaction mixture was degassed using 4 cycles of vacuum and nitrogen refilling. The reaction was heated at 110 C for 24 h then cooled to room temperature. Silica gel was added and the solvent was removed under vacuum. The desired product was purified by silica gel chromatography (eluting with hexanes/ ethyl acetate methanol). The title compound was obtained as a solid (350 rng). LCMS M/Z (M+H) 293.

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics