Category: 92525-10-5

Reference of 92525-10-5, The chemical industry reduces the impact on the environment during synthesis 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Step 1-Synthesis of 2-(1-methyl-1H-pyrazol-3-yl)-4-(trimethylsilyl)but-3-yn-2-ol To a solution of 3-iodo-1-methyl-1H-pyrazole (378 mg, 1.82 mmol) in dry DCM (15 mL) at 0 C. under an atmosphere of nitrogen, was introduced ethylmagnesium bromide (2.0 mL of a 1.0M solution in THF, 2.0 mmol). After 30 minutes at 0 C., the reaction mixture was warmed to RT for 15 minutes, then introduced to a solution of 4-(trimethylsilyl)but-3-yn-2-one (0.37 ml, 2.18 mmol) in dry DCM (5 ml) at 0 C. under an atmosphere of nitrogen. The reaction mixture was warmed to RT for 16 hr. Following addition of saturated aqueous ammonium chloride (5 ml), the reaction mixture was extracted with DCM (3*5 mL extractions). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography (heptane/EtOAc gradient) furnished the title compound as an orange-brown oil: 1H NMR (500 MHz, CDCl3) delta 0.15 (9H, d, J=3.5 Hz), 1.82 (3H, s), 3.18 (1H, s), 3.86 (3H, s), 6.28 (1H, d, J=2.2 Hz), 7.26 (1H, d, J=2.2 Hz); LC-MS: m/z=+222.95 (M+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, 3-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

92525-10-5, name is 3-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. Safety of 3-Iodo-1-methyl-1H-pyrazole

A) A solution of 3-iodo-1-methyl-1H-pyrazole (200 mg), 3,3-dimethylpyrrolidin-2-one (109 mg), copper(I) iodide (73 mg), N1,N2-dimethylethane-1,2-diamine (0.083 mL) and tripotassium phosphate (408 mg) in cyclopentyl methyl ether (4 mL) was stirred overnight at 120 C. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (170 mg). MS (ESI+): [M+H]+: 194.1

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Yoshida, Masato; TAKAMI, Kazuaki; TOMINARI, Yusuke; SHIOKAWA, Zenyu; SHIBUYA, Akito; SASAKI, Yusuke; GIBSON, Tony; TAKAGI, Terufumi; US2015/133451; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, These common heterocyclic compound, 92525-10-5, name is 3-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.

3-Iodo-1-methyl-1H-pyrazole (2.19 g, 10.5 mmol) was added dropwise to iPrMgCl.LiCl (10.8 mL, 14.0 mmol, 1.3 M THF solution) and THF (14 mL) cooled to 0 C. under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 1 h. N-Methoxy-N,1-dimethylcyclopentane-1-carboxamide (1.2 g, 7.0 mmol) was then added dropwise. The mixture was stirred at room temperature for 18 h and then was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc. The organic extract was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10-50% EtOAc/heptane) to afford 992 mg (74%) of the title compound. LCMS 172.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.34 (d, J=2.3 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 3.98 (s, 3H), 2.46-2.33 (m, 2H), 1.79-1.63 (m, 6H), 1.49 (s, 3H).

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Gerstenberger, Brian Stephen; Flick, Andrew Christopher; Lombardo, Vincent Michael; Mousseau, James John; Nuhant, Philippe Marcel; Robinson, JR., Ralph Pelton; Schnute, Mark Edward; Kung, Daniel Wei-Shung; Schmitt, Daniel Copley; Thorarensen, Atli; Trujillo, John Isidro; Unwalla, Rayomand Jal; Wu, Huixian; (104 pag.)US2020/95239; (2020); 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Iodo-1-methyl-1H-pyrazole

Step 1. Synthesis of 5-fluoro-3-iodo-1-methyl-1H-pyrazole (C27) Lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 3.30 mL, 6.60 mmol) was added drop-wise to a -75 C. solution of 3-iodo-1-methyl-1H-pyrazole (97%, 1.29 g, 6.02 mmol) in tetrahydrofuran (25 mL). After 5 minutes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (97%, 2.60 g, 8.00 mmol) was added to the cold solution in one portion. The reaction mixture was allowed to warm to 0 C. over 30 minutes, and was then quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) afforded the product as a pale yellow oil. Yield: 435 mg, 1.92 mmol, 32%. GCMS m/z 226 [M+]. 1H NMR (400 MHz, CDCl3) delta 5.93 (d, J=6.0 Hz, 1H), 3.74 (d, J=1.2 Hz, 3H).

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 92525-10-5.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Butler, Christopher Ryan; Beck, Elizabeth Mary; Davoren, Jennifer Elizabeth; LaChapelle, Erik Alphie; O’Neill, Brian Thomas; US2014/228356; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, These common heterocyclic compound, 92525-10-5, name is 3-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.

3-Iodo-1-methyl-1H-pyrazole (2.19 g, 10.5 mmol) was added dropwise to iPrMgCl.LiCl (10.8 mL, 14.0 mmol, 1.3 M THF solution) and THF (14 mL) cooled to 0 C. under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 1 h. N-Methoxy-N,1-dimethylcyclopentane-1-carboxamide (1.2 g, 7.0 mmol) was then added dropwise. The mixture was stirred at room temperature for 18 h and then was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc. The organic extract was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10-50% EtOAc/heptane) to afford 992 mg (74%) of the title compound. LCMS 172.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.34 (d, J=2.3 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 3.98 (s, 3H), 2.46-2.33 (m, 2H), 1.79-1.63 (m, 6H), 1.49 (s, 3H).

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Gerstenberger, Brian Stephen; Flick, Andrew Christopher; Lombardo, Vincent Michael; Mousseau, James John; Nuhant, Philippe Marcel; Robinson, JR., Ralph Pelton; Schnute, Mark Edward; Kung, Daniel Wei-Shung; Schmitt, Daniel Copley; Thorarensen, Atli; Trujillo, John Isidro; Unwalla, Rayomand Jal; Wu, Huixian; (104 pag.)US2020/95239; (2020); 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Iodo-1-methyl-1H-pyrazole

Step 1. Synthesis of 5-fluoro-3-iodo-1-methyl-1H-pyrazole (C27) Lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 3.30 mL, 6.60 mmol) was added drop-wise to a -75 C. solution of 3-iodo-1-methyl-1H-pyrazole (97%, 1.29 g, 6.02 mmol) in tetrahydrofuran (25 mL). After 5 minutes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (97%, 2.60 g, 8.00 mmol) was added to the cold solution in one portion. The reaction mixture was allowed to warm to 0 C. over 30 minutes, and was then quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) afforded the product as a pale yellow oil. Yield: 435 mg, 1.92 mmol, 32%. GCMS m/z 226 [M+]. 1H NMR (400 MHz, CDCl3) delta 5.93 (d, J=6.0 Hz, 1H), 3.74 (d, J=1.2 Hz, 3H).

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 92525-10-5.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Butler, Christopher Ryan; Beck, Elizabeth Mary; Davoren, Jennifer Elizabeth; LaChapelle, Erik Alphie; O’Neill, Brian Thomas; US2014/228356; (2014); 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C4H5IN2

A degassed solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one (27 mg, 0.100 mmol), 3-iodo-1-methyl-1H-pyrazole (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (4 mg, 0.020 mmol), and potassium phosphate (43 mg, 0.197 mmol) 2 mL of N-methylpyrrolidone was heated to 70 C. After allowing the reaction to stir overnight (17 h) at 70 C., the reaction was complete and allowed to cool to room temperature. The reaction was extracted 3X’s with EtOAc (3*5 mL) and 2X’s with NaHCO3 (3*10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and then concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using a 0-100% EtOAc/100-0% Hexane gradient mixture. A second column was done on the impure product using a gradient of MeOH/CHCl3 after which, the appropriate fractions were concentrated, to afford a yellow solid (17 mg, 52%). 1H NMR (DMSO) delta: 8.01 (s, 1H), 7.79 (d, J=6.0, 1H), 6.34 (d, J=6.0, 1H), 6.24 (m, 1H), 6.15 (d, J=7.0 Hz, 2H), 4.00 (br. S, 2H), 3.22 (s, 2H), 2.64 (t, j=5.3 Hz, 2H), 2.20 (s, 3H)

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; Allergan, Inc.; Wurster, Julie; Yee, Richard; Hull III, Clarence Eugene; Malone, Thomas C.; (39 pag.)US2016/96832; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, 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. 92525-10-5 name is 3-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.

A suspension of 3 ,3-dimethyl-6- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one (200 mg) and 5-bromo-2-methylpyrimidine (181 mg) in 1,4-dioxane (2 ml) and aqueous sodiumcarbonate (2 M) was flushed with argon, then [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (26 mg) was added and stirring was continued at 115 C for 3 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (148 mg, 84%) as a brown solid. MS (mlz): 254.2 [(M+H) :_The title compound was prepared in analogy to example ic using 3,3-dimethyl-6-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one from example lb and 3-iodo- i-methyl-i Hpyrazole to give the title compound (26%) as an off-white solid. MS (mlz): 242.1 [(M+H)?i.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 92525-10-5, 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of the ail above brown solid, Pd(PPh3 )2Cl2 (31 mg, 0.044 mmol) and Cu l (8 mg, 0.044 mmol) in DMF (2 mL) under N2 atmosphere was added a solution of 3-iodo-l – methyl- 1 f-pyrazole (170 mg, 0.817 mmol) and triethylamlne (179 mg, 1.77 mmol) in DMF (1 .5 mL), The resulted mixture was heated to 80 C and stirred further for 16 hours, then diluted with EtOAc (20 mL) and washed with water (20 mL x 2) and brine (20 mL). The separated organic phase was concentrated in vacuo and the residue was suspended in a mixture of PE/EtOAe (5/1 (v/v), 12 mL). The mixture was stirred at rt for 4 hours, then filtered and the filter cake was washed with PE (10 mL). The filter cake was dried in vacuo to give the title compound as an orange-yellow solid (139 mg, yield for two steps (Step 4 and Step 5): 72.8%). MS (ESI, pos. ion.) m/z: 234.1 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-Lambda) delta (ppm): 8.22 (s, 1H), 7.79 (d, J = 2.2 Hz, 1H), 6.64 (d, J = 2.2 Hz, 1H), 3.89 (s, 3H).

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

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 92525-10-5, name is 3-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 92525-10-5, Quality Control of 3-Iodo-1-methyl-1H-pyrazole

H) 3-amino-5-(2-methylcyclohexyl)-7-(1-methyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one A mixture of 3-amino-7-bromo-5-(2-methylcyclohexyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step G (200 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (861 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (22.0 mg), potassium acetate (121 mg) and N,N-dimethylformamide (3.0 mL) was heated with microwave irradiation at 110C for 5 hr. The reaction mixture was cooled to room temperature, and 3-iodo-1-methyl-1H-pyrazole (384 mg), aqueous sodium carbonate solution (2 M, 0.610 mL) and tetrakis(triphenylphosphine)palladium(0) (71.0 mg) were added thereto at room temperature. The reaction mixture was heated with microwave irradiation at 140C for 1 hr. The reaction mixture was cooled to room temperature, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/dichloromethane) to give the title compound (51.0 mg). 1H NMR (400 MHz, CDCl3) delta 0.78-0.88 (3H, m), 1.24-2.04 (9H, m), 3.96 (3H, brs), 4.74-4.77 (2H, m), 6.40-6.45 (1H, m), 7.33-7.37 (1H, m), 7.39-7.40 (1H, m), 10.45 (1H, brs). MS (ESI+): [M+H]+327.3.

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics