Category: 39806-90-1

Electric Literature 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

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.

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

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, Formula: C4H5IN2

Step 1: Prepartion of tert-but 4-(l-methyI-lH-pyrazoI-4-yl)-3-oxopiperazine~l- carboxylate: tot-Butyl 3-oxopiperazine-l-carbox late (0.164 g, 0.819 mmol) was suspended in isopropanol (3 mL) under an atmosphere of nitrogen and treated with l-methyl-4-iodo-lH- pyrazole (0.204 g, 0.983 mmol, 1.20 equiv), ethylene glycol (0.051 g, 0.82 mmol, 1.0 equiv). copper iodide (0.03 g, 0.16 mmol, 0.20 equiv), and potassium phosphate (0.695 g, 3.28 mmol, 4.00 equiv), and placed into a preheated oil bath at 100 C for 8 hours. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was dissolved in dichloromethane, washed with water, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 0: 100 hexanes : ethyl acetate), providing the titled compound.

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; MERCK SHARP & DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2011/137049; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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.

To a solution of l-methyl-4-iodo- lH-pyrazole (3 g, 14.42 mmol) in THF (40 mL) was added isopropylmagnesium chloride (2.0M in THF, 8.00 mL, 16.01 mmol) at O 0C. The mixture was stirred at O 0C for 1 h, cooled to -78 0C and JV-methoxy-Lambda’-methyl-2- ethoxyacetamide (product of Step A, 3.18 g, 21.63 mmol) was added. The mixture was slowly warmed to rt over 1.5 h. The reaction was cooled to -78 0C and quenched by the dropwise addition of saturated aqueous NH4CI. The reaction was warmed to rt and stored in the cold overnight. The reaction was then diluted with cold IN HCl, extracted four times with EtOAc, and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography eluting with a gradient of 50% EtOAc/hexanes to 100% EtOAc afforded 2-ethoxy-l-(l-methyl-pyrazol-4-yl)-ethanone. 1H NMR (500 MHz, CDCl3): 6 8.07(s, IH), 8.03 (s, IH), 4.38 (s, 2H), 3.96 (s, 3H), 3.62 (q, 2H), 1.29 (t, 3H).

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:
Patent; MERCK SHARP & DOHME CORP.; GUO, Liangqin; LIU, Jian; NARGUND, Ravi, P.; PASTERNAK, Alexander; YANG, Lihu; YE, Zhixiong; WO2010/51177; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 4-Iodo-1-methyl-1H-pyrazole

4-lodo-1-methyl-1H-pyrazole (1.12 g; 5.385 mmol) and 4-(Methoxy-methyl- carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.47 g; 5.385 mmol) were dissolved in dry THF (15 mL) under argon. While stirring the clear light yellow solution was cooled down to -60 C and butyllithium (15% solution in n- hexane) (3.72 mL; 5.923 mmol) was added dropwise at this temperature over a period of 10 min. The reaction mixture was stirred for 30 min between -60 and -45 C, then slowly warmed to room temperature and stirred for 14 h. The reaction mixture was cooled to 0 C, quenched with 0% citric acid solution, diluted with ethyl acetate (70 mL) and washed with water and brine, dried with Na2S04) filtered and evaporated to dryness. The oily residue was purified by flash chromatography (Companion RF; 120 g Si50 silica gel column); yield: 999 mg (63%) light green oil (purity: 99.4; Rt: 2.33 min); 1H NMR (500 MHz, DMSO-d6) delta 8.42 (s, 1H), 7.94 (d, J = 0.7 Hz, 1H), 3.97 (d, J = 12.6 Hz, 2H), 3.87 (s, 3H), 3.15 (tt, J = 11.4, 3.6 Hz, 1 H), 2.93 – 2.75 (m, 2H), 1.76 – 1.67 (m, 2H), 1.33-1.46 (m, 1 H); LC/MS (C), Rt: 1.93 min; 238.1 (M+H; BOC-cleaved mass).

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

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; BUCHSTALLER, Hans-Peter; WO2015/14442; (2015); 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A solution of 4-iodo-1-methyl-1H-pyrazole (0.80 g, 3.9 mmol) in THF (7.04 g, 8.00 ml, 98 mmol) was cooled at 0 C. A solution of isopropylmagnesium chloride lithium chloride complex in THF (5.42 ml, 4.23 mmol, 0.78 molar) was added dropwise and the reaction was stifled for 1 hour. A solution of N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (0.733 g, 4.23 mmol) in THF (2 mL) was added dropwise. Cooling was removed after 15 min and reaction was then stirred for 2 hours. To the mixture was added 2 M HCl (20 mL) and it was extracted with AcOEt (3×25 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to yield (1-methyl-1H-pyrazol-4-yl)(tetrahydro-2H-pyran-4-yl)methanone (220 mg, 1.13 mmol, 29.4% yield). [0365] 1H NMR (600 MHz, CDCl3) delta 7.87 (s, 1H), 7.87 (s, 1H), 4.03 (ddd, J=11.4, 4.1, 2.4 Hz, 2H), 3.92 (s, 3H), 3.49 (td, J=11.7, 2.3 Hz, 211), 3.06 (tt, J=11.3, 3.8 Hz, 1H), 1.86 (dtd, J=13.8, 11.7, 4.4 Hz, 2H), 1.72 (ddd, J=13.4, 3.7, 2.0 Hz, 2H)

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

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39806-90-1, 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. 39806-90-1 name is 4-Iodo-1-methyl-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 a solution of 4-iodo-l-methyl-lH-pyrazole (10.20 mg, 0.049 mmol) in anhydrous DMSO (5 ml) was added common intermediate D.2 (10 mg, 0.033 mmol), (Irans)-N I N2- dimethylcyclohexane-l, 2-diamine (0.930 mg, 6.54 mhio). potassium phosphate (20.82 mg, 0.098 mmol) and Cul (0.623 mg, 3.27 pmol). The resulting mixture was stirred at 90C under N2 atmosphere for 12 hours. LCMS showed the starting material was consumed. After filtration and concentration, the crude product was purified by pre-HPLC (TFA) to give example 7.1, 5-chloro- l-(l-methyl-lH-pyrazol-4-yl)-6-(l-(3-methyloxetan-3-yl)piperidin-4-yl)-lH-indazole, TFA salt. MS (ESI) m/z calc?d for C20H25CIN5O [M+H]+ 386, found 386. NMR (400 MHz, CD3OD) d 8.15 (s, 1H), 8.13 (s, 1H), 7.94 (s, 1H), 7.86 (s, 1H), 7.50 (s, 1H), 4.92 (m, 3H), 4.49 (d, J = 7.83 Hz, 2H), 4.01 (s, 3H), 3.52-3.66 (m, 1H), 3.38-3.48 (m, 3H), 3.33 (br s, 1H), 2.30 (m, 2H), 2.08- 2.18 (m, 2H), 1.79 (s, 3H). LRRK2 ICso 1.4 nM.

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.

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.

A suspension of 5-chloro-lH-pyrazolo[3,4-c]pyridine (300 mg, 1.95 mmol), 4- iodo-l-methylpyrazole (600 mg, 2.88 mmol), 2-isobutyrylcyclohexanone (130 mg, 0.773 mmol), copper(I) iodide (75 mg, 0.39 mmol) and cesium carbonate (1.5 g, 4.60 mmol) in 5 mL of DMA was deoxygenated by bubbling nitrogen for 15 min. Next, the reaction mixture was warmed to (0809) 100C and stirred overnight. The reaction mixture was then cooled and diluted with DCM, washed with 1 N aqueous NaOH and water, dried (Na2S04) and concentrated to dryness. The solid residue was suspended in ether and filtered to collect the desired intermediate, 5-chloro-l- (0810) (l-methyl-lH-pyrazol-4-yl)-lH-pyrazolo[3,4-c]pyridine: MS (EI) calc’d for Ci0H9ClN5 [M+H]+ (0811) 234, found 234; 1H NMR (600 MHz, OMSO-d6) delta 9.02 (s, 1 H), 8.41 (s, 1 H), 8.38 (s, 1 H), 7.97 (0812) (s, 1 H), 7.96 (s, 1 H), 3.91 (s, 3 H)

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

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

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. name: 4-Iodo-1-methyl-1H-pyrazole

Step 2: l -methyl-l H-pyrazole-4-carbonitrile To a solution of 4-iodo- l -methyl- 1 H-pyrazole (55 gm, 0.264 moles) in N,N- dimethylacetamide ( 100 ml) was added 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). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90- 1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min 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 off, washed with cold DI water (100 ml) and dried at 40-50 C to yield the product, 1 -methyl- l H-pyrazole-4-carbonitrile,. Dry wt : 17.94 gm Yield : 0.32 w/w (63%);

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