Some tips on Ethyl 4-iodo-1H-pyrazole-5-carboxylate

According to the analysis of related databases, 179692-08-1, the application of this compound in the production field has become more and more popular.

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 179692-08-1 as follows. name: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium (II)bis(triphenylphosphine) dichloride (0.05eq) and boronic acid or pinnacol ester (1.2eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3mL/mmol) and a 1M aqueous solution of Sodium Carbonate (3eq) were added. The vessel was capped and heated thermally 3-18hrs at 100C. Upon completion, the reaction was cooled and crude product was either triterated via addition of water and collection by filtration or extracted with sat ammonium chloride and DCM. If the crude product was an intermediate, it was taken into the next step in most cases w/o further purification or alternatively submitted for reverse phase HPLC purification when it was a final product.Similar to the procedure as described in General Procedure M, ethyl 4-iodo-lH- pyrazole-3-carboxylate was reacted with 1 -ethyl- lH-pyrazol-4-ylboronic acid to give the title compound (343 mg, 27%) as a yellow oil. LC-MS (ES, m/z): 235 [M+H]+.

According to the analysis of related databases, 179692-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Share a compound : C4H3N3

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.

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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 1H-Pyrazole-4-carbonitrile

To a suspension of 1H-pyrazole-4-carbonitrile (50.5 mg, 0.542 mmol), K3P04(233 mg, 1.084 mmol) and 6-(3-chloro-2-fluoro-6-iodophenyl)pyrimidin-4-ol (190 mg,0.542 mmol) in dioxane (0.24 mL) was added (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (38.6 mg, 0.271 mmol). The vial was then purged with Ar, Cul (5.16 mg, 0.027mmol) was added, and the vial was sealed. The reaction mixture was heated at 80 C.After 16 h, the reaction was cooled to rt, filtered, and the filtrate was concentrated. Purification by reverse phase chromatography gave 1 -(4-chloro-3 -fluoro-2-(6-hydroxypyrimidin-4-yl)phenyl)- 1 H-pyrazole-4-carbonitrile (74 mg, 43% yield) as an offwhite solid. MS(ESI)m/z: 316.3 (M+H). ?H NMR (400MHz, CD3OD) oe 8.54 (s, 1H),8.09 (d, J=0.9 Hz, 1H), 7.97 (s, 1H), 7.80 (dd, J=8.7, 7.8 Hz, 1H), 7.50 (dd, J=8.7, 1.7 Hz, 1H), 6.51 (t,J1.1 Hz, 1H).

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; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A new synthetic route of 20583-33-9

Statistics shows that 1-(1H-Pyrazol-3-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 20583-33-9.

Application of 20583-33-9, These common heterocyclic compound, 20583-33-9, name is 1-(1H-Pyrazol-3-yl)ethanone, 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.

Pyrazole viii (30 g, 0.27 mol) and cesium carbonate (98 g, 0.30 mol) are dissolved in dimethyiformamide (DMF) (300 niL). 2-Bromopropane (30 mL, 0.32 mol) is added dropwise and the mixture is stirred for 12 hours. The mixture is poured onto water (1 L) and extracted into ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and (0154) concentrated to give substituted pyrazole ix (22 g, 0.14 mol) as a pale yellow liquid winch is used without further purification.

Statistics shows that 1-(1H-Pyrazol-3-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 20583-33-9.

Reference:
Patent; CLAVIUS PHARMACEUTICALS, LLC; SAWYER, J. Scott; (132 pag.)WO2020/41562; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 4-Iodo-1-methyl-1H-pyrazole

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.

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

A new synthetic route of C3H5N3

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 28466-26-4.

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. 28466-26-4, name is 4-Aminopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 28466-26-4

Compound 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (206 mg, 1 mmol),1H-pyrazole-4-amine (83mg, 1mmol),Diisopropylethylamine (258mg, 2mmol)Mix with ethanol (20 mL), heat to 80 C and stir for 2 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol = 19/1).The target product 4-((1H-pyrazol-4-yl) amino) -6-chloropyridazine-3-carboxylic acid methyl ester 41a (150 mg, yellow solid) was obtained,Yield: 59%.

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 28466-26-4.

Reference:
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some scientific research about C6H7BrN2O2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-bromo-1H-pyrazole-4-carboxylate, its application will become more common.

Synthetic Route of 1353100-91-0,Some common heterocyclic compound, 1353100-91-0, name is Ethyl 3-bromo-1H-pyrazole-4-carboxylate, molecular formula is C6H7BrN2O2, 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 NaH (275 mg, 6.86 mmol, 60% purity) in THF (5 mL) was added dropwise a solution of ethyl 3-bromo-lH-pyrazole-4-carboxylate (1.0 g, 4.57 mmol) in THF (10 mL) at 0 C. After addition, the mixture was stirred at this temperature for lh, and then Mel (2.93 g, 20.64 mmol, 1.29 mL) was added dropwise at 0 C. The resulting mixture was stirred at 25 C for 19h. The reaction mixture was quenched by addition sat. H4CI (5 mL), and then diluted with H20 (10 mL) and extracted with EtOAc (20 mL x 2). The combined organic layers were washed with brine (15 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 8/1 to 5: 1) to give the Compound 142A (120 mg, yield: 11.27%) was obtained as a yellow oil and Compound 142B (370.00 mg, yield: 34.74%) was obtained as a white solid. (1387) [0574] 1H NMR (400MHz, CDC13) (142A) delta 7.93 (s, 1H), 4.42 – 4.21 (m, 2H), 3.97 – 3.82 (m, 3H), 1.36 (t, J = 7.2 Hz, 3H) (1388) [0575] 1H NMR (400MHz, CDC13) (142B) delta 7.83 (s, 1H), 4.30 (q, J = 7.0 Hz, 2H), 3.94 – 3.86 (m, 3H), 1.41 – 1.28 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-bromo-1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; MA, Jingyuan; EMAYAN, Kumaraswamy; ADLER, Marc; (327 pag.)WO2018/9417; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sources of common compounds: 3524-32-1

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.

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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., name: 5-Amino-1,3-dimethylpyrazole

Example 57 2-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide To a 10 mL microwave tube was added 2-(2-chloro-5-isopropenyl-pyridin-4-ylamino)-N-methyl-benzamide (0.075 g, 0.25 mmol, 1 eq), 2,5-dimethyl-2H-pyrazol-3-ylamine (0.055 g, 0.50 mmol, 2 eq), Cs2CO3 (0.24 g, 0.74 mmol, 3 eq) and 1,4-dioxane (3 mL). The resulting mixture was degassed with N2 for 30 minutes. Then Pd(OAc)2 (0.015 g, 0.07 mmol, 0.27 eq) and BINAP (0.046 g, 0.074 mmol, 0.3 eq) were added and the mixture degassed again with N2 for another 10 minutes. The resulting reaction mixture was irradiated in a CEM microwave at 110 C. and 150 W for 45 min. The progress of the reaction was monitored by LCMS. After it was complete, Cs2CO3 was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by column chromatography over neutral alumina using 0.2% MeOH-DCM as the eluant. This gave the title compound as an off white solid (180 mg, 48%). 1H-NMR (400 MHz, DMSO-d6): delta 2.02-2.10 (m, 6H), 2.73-2.74 (d, 3H, J=4.48 Hz), 3.53 (s, 3H), 5.05 (s, 1H), 5.31 (s, 1H), 5.97 (s, 1H), 6.67 (s, 1H), 6.90-7.05 (m, 1H), 7.4-7.55 (m, 2H), 7.61-7.63 (d, 1H, J=7.04 Hz), 7.76 (s, 1H), 8.48 (s, 1H), 8.54-8.67 (brs, 1H), 9.61 (s, 1H). LC-MS [M+H]+=377.4.

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; ADAMS, Jerry Leroy; Faitg, Thomas H.; Johnson, Neil W.; Lin, Hong; US2010/113475; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Discovery of 95162-14-4

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-Bromo-1-tritylpyrazole, other downstream synthetic routes, hurry up and to see.

Related Products of 95162-14-4, 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. 95162-14-4, name is 4-Bromo-1-tritylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A stirred mixture of 5.0 g (12.8 mmol) of 4-bromo-1-trityl-1H-pyrazole, 9.8 g (38.6 mmol, 3.0 eq.) of bis(pinacolato)diboron, 1.0 g (1.3 mmol, 10 mol %) of PdCl2(dppf) and 6.3 g (64.2 mmol, 5.0 eq) of potassium acetate in DMF (30 mL) was heated at 80 C. for 16 h. The resulting mixture was diluted with water, and the product was extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and purified by flash chromatography to give 5.1 g (91%) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole.

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-Bromo-1-tritylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bentzien, Joerg Martin; Takahashi, Hidenori; US2008/261975; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sources of common compounds: 39806-90-1

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

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

Some tips on 28466-26-4

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Synthetic Route of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

A mixture of N-(2-chloropyrimidin-4-yl)-l-isopropyl-lH-imidazo[4,5-c]pyridin-6-amine (Example 12, Step 4) (51.1 mg, 0.177 mmol), lH-pyrazol-4-amine (23.9 mg, 0.288 mmol), trifluoroacetic acid (10.0 mu^, 0.129 mmol) and fert-butanol (1.5 mL, 16 mmol) was heated in a sealed vial at 100 C for 2 days. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product (20.3 mg) was purified via reverse-phase HPLC and lyophilized to yield 4.6 mg (8%) of the title compound. LCMS (ESI): RT (min) = 3.051, [M+H]+ = 336.2, method = B; lH NMR (400 MHz, DMSO-d6) delta 12.43 (s, 1H), 9.72 (s, 1H), 8.83 (s, 1H), 8.66 (d, J = 1.0 Hz, 1H), 8.38 (s, 1H), 8.01 (d, J = 5.7 Hz, 1H), 6.67 (s, 1H), 4.62 (br s, 1H), 1.51 (d, J = 6.6 Hz, 6H).

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics