Tag: M.W:100-200

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. 214614-81-0, name is 4-Bromo-1-(2-hydroxyethyl)pyrazole, A new synthetic method of this compound is introduced below., Product Details of 214614-81-0

General procedure: To a solution of 4-bromo-1-(oxan-4-yl)-1H-pyrazole 26a (1.00 g, 4.33 mmol) and 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.32 g, 5.19 mmol) in 10 mL of DMF was added potassium acetate (1.27 g, 12.98 mmol), followed by 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (177 mg, 0.22 mmol) under argon. The resulting mixture was stirred at 80 C for 10 h and then diluted with 40 mL of water. The mixture was extracted with EA (3 × 30 mL). The combined organic phase was washed with water (3 × 30 mL), brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography (EA/PE, 1:4) to afford 25c as white solid in 68% yield.

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:
Article; Zhang, Dengyou; Zhang, Xiaowei; Ai, Jing; Zhai, Yun; Liang, Zhongjie; Wang, Ying; Chen, Yi; Li, Chunpu; Zhao, Fei; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6804 – 6820;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4027-57-0, These common heterocyclic compound, 4027-57-0, name is Ethyl 5-methylpyrazole-3-carboxylate, 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.

Reference 4; Preparation of 3-formyl-5-methylpyrazole; Under nitrogen environment, 3-ethoxycarbonyl-5-methylpyrazole (1.0 g, 4.34 mmol) was dissolved in 15 ml of purified toluene, and DIBAL (8.68 ml, 8.62 mmol) was slowly added and stirred at -78 C. The reaction progress and completion were confirmed using TLC (hexane:EtOAc=6:1). Upon completion of the reaction, MeOH and water were slowly added to the reaction mixture and the resulting mixture was filtered through a celite bed, and the aqueous layer was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:1) to obtain the title compound. Yield: 82.4% 1H NMR (300 MHz, CDCl3) delta 9.92 (s, 1H), 6.68 (s, 1H), 2.82 (s, 3H)

Statistics shows that Ethyl 5-methylpyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 4027-57-0.

Reference:
Patent; Korea Institute of Science and Technology; US2007/49604; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 821767-61-7,Some common heterocyclic compound, 821767-61-7, name is tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, molecular formula is C9H12N2O3, 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 a N2 flow, to a solution of intermediate 11(202 mg, 0.62 mmol) in DCM (10 mL) was added tert-butyl 4-formyl-1H-pyrazole-1-carboxylate (133 mg, 0.68 mmol) andAcOH (35 jiL, 0.62 mmol). The mixture was stirred at room temperature for 2h.NaBH(OAc)3 (521 mg, 2.46 mmol) was added and the mixture was stirred at rt overnight,poured into ice water and the layers were separated. The aqueous layer was extractedwith DCM. The organic layers were combined, washed with brine then dried overMg504, evaporated. The residue was purified by chromatography over silica gel(stationary phase: irregular SiOH 15-40jim 24g, mobile phase: DCM/MeOH(+10% NH4OH): 97/3). The pure fractions were mixed and evaporated yielding 145 mg (yield 46%) of intermediate 50.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, 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 920006-32-2, category: pyrazoles-derivatives

Example 100 N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide To a solution of HATU (0.253 g) in DMF (3 ml) was added 1-(1-methylethyl)-1H-pyrazole-5-carboxylic acid (0.102 g) and DIPEA (0.211 ml) and the mixture was left to stand for 10 min. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (0.075 g) dissolved in DMF (3 ml) was added and the solution was left to stand at RT for 18 h. DMF was removed by blow down (not to dryness) and the residue was dissolved in chloroform (1 ml) and loaded onto an aminopropyl SPE (2 g) (pre-conditioned with methanol (6 ml) and chloroform (6 ml)). The mixture was left on the column for 2 h then eluted with ethyl acetate:methanol (1:1, 10 ml). The solvent was blown down to dryness and the residue was dissolved in DMSO:methanol (1 ml, 1:1) and purified by MDAP (method K). The solvent was removed in vacuo and dried in an vacuum oven (50 C.) overnight to give title compound, 18 mg. LCMS (method B) R=3.23 mi MH=385.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropylpyrazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001020-17-2,Some common heterocyclic compound, 1001020-17-2, name is 3-(tert-Butyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C8H12N2O, 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.

Example 78 2-(2-(3-7erf-butyl-4-formyl-1H-pyrazol-1-vnacetan?ido)-N-nnethyl-4,5.6,7- tetrahvdrobenzofblthiophene-3-carboxannide3-Terf-butyl-1H-pyrazole-4-carbaldehyde (150 mg, 0.986 mmol), 2-(2-bromoacetamido)- N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxannide (490 mg, 1.478 mmol) and potassium carbonate (545 mg, 3.94 mmol) were mixed with DMF (5 ml_) and heated for 3 h at 60 0C. The reaction was partitioned between water and EtOAc. Organics were combined and purified by chromatography (0-60%, EtOAc/heptane) to give the title product as a white solid (360 mg, 0.894 mmol, 91 %). MS (ESI): m/z 403.6 [M + H]+.

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

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); 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. 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Under argon, 3-(4-bromopyrazol-1-yl)pyridine (1.00 g, 4.46 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (dppf) (74 mg, 0.13 mmol), palladium dichloride-dppf (109 mg, 0.13 mmol), potassium acetate (1.31 g, 13.3 mmol) and pinacolatodiborane (1.19 g, 4.68 mmol) were added to dioxane (11 ml). The mixture was heated under reflux for 24 h and then cooled. The solvent was removed on a rotary evaporator under reduced pressure, dichloromethane (100 ml) and water (100 ml) were added to the residue, and the solids formed were filtered off with suction and discarded. The filtrate was extracted with dichloromethane and the organic phase was dried over magnesium sulphate. The solvent was removed on a rotary evaporator under reduced pressure and the residue was chromatographed (ethyl acetate, cyclohexane).Yield: 680 mg (55% of theory), logP(HCOOH) 2.19, [M++1] 272.21H NMR (d6-DMSO): 1.30 (s, 12H), 7.51 (m, 1H), 7.90 (s, 1H), 8.25 (m, 1H), 8.51 (m, 1H), 8.73 (s, 1H), 9.12 (m, 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; BAYER CROPSCIENCE AG; US2012/165345; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 89260-46-8,Some common heterocyclic compound, 89260-46-8, name is 3-(1H-Pyrazol-3-yl)aniline, molecular formula is C9H9N3, 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.

(2S)-N-(3-(lH-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide (12.C).To a solution of 3-(lH-pyrazol-3-yl)benzenamine 12.B (400 mg, 2.52 mmol) in DMF (5 mL) was added (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (795 mg, 3.02 mmol, available from Aldrich), diisopropylethylamine (0.65 mL, 3.75 mmol) and 2-(1H- Benzotriazole-l-yl)-l,l,3,3-Tetramethyluronium hexafluorophosphate (1.14g, 3.02 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was then partitioned between water (50 mL) and EtOAc (50 mL). The layers were separated and the aqueous phase was extracted with additional EtOAc (2 x 5OmL). The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. [0253] The crude intermediate was then stirred in HCl solution (4M in dioxane, 5 mL) for Ih. The mixture was then concentrated, the resulting white solid was neutralized with NaHCO3 saturated solution (5 mL) and extracted with DCM (2 x 5mL) to afford (2S)-N-(3- (lH-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide 12.C as a colorless film (200mg, 26% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1H-Pyrazol-3-yl)aniline, its application will become more common.

Reference:
Patent; AMGEN INC.; DU, Xiaohui; FU, Zice; HOUZE, Jonathan, B.; JIAO, Xianyun; KIM, Yong-jae; LI, Leping; LIU, Jinqian; LIZARZABURU, Mike; MEDINA, Julio; SHEN, Wang; TURCOTTE, Simon; YU, Ming; WO2010/93849; (2010); A2;,
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. 1072-91-9, name is 1,3,5-Trimethylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3,5-Trimethylpyrazole

1,3, 5-Trimethyl-lH-pyrazole (630 mg, 5.71 mmol) cooled to [0 oC] was treated with oxalyl chloride (7.0 mL). The reaction was then warmed to [25 oC] and then heated to reflux for 4 h. At this time, the reaction was cooled to [25 oC] and was stirred at [25 oC] for 24 h. At this time, the excess oxalyl chloride was removed by distillation. The resulting residue was cooled to [0 oC] and treated with ice/water (15 mL). The mixture was slowly warmed to [25 oC] over 4 h. At this time, the resulting solids were collected by filtration, washed with water, and dried in vacuo to afford [OXO- (1,] 3,5- [TRIMETHYL-LH-PYRAZOL-4-YL)-ACETIC] acid (700 mg, 70%) as brown solid

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; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 10250-59-6, name is Methyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, molecular formula is C7H10N2O2, 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. HPLC of Formula: C7H10N2O2

Example 1 : Preparation of N-(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-4-(5-trifluormethyl- pyridin-2-yloxy)-benzenesulfonamide (Table I: example 1-21 )Example 1.1 : Preparation of (2,5-dimethyl-2H-pyrazol-3-yl)-methanol At 25 to 300C 25 ml of a 1 molar solution of lithium aluminium hydride in diethylether was added dropwise to 4.5 g 2,5-dimethyl-2H-pyrazole-3-caboxylic acid methyl ester in 50 ml diethylether. A solid precipitated and the reaction mixture was stirred for about 2 to 3 days at about 20 to 25C. After dilution of the reaction mixture with 50 ml of MTBE a little volume of water was added. After filtration the precipitated wet solid was thoroughly washed with ethyl acetate. The solvent was removed in vacuo from the combined filtrate and washing fluids to yield 3.7 g of the title compound. 1H-NMR (CDCI3, delta in ppm): 5.9 (s, 1 H); 4.6 (s, 2H); 4.0 (s, broad, 1 H); 3.75 (s, 3H); 2.2 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10250-59-6, its application will become more common.

Reference:
Patent; BASF SE; WO2009/101082; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 873191-23-2, 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 873191-23-2 as follows.

General procedure: The phenanthridine skeletons1-8 (0.1 mmol) were dissolved in dryTHF (10 mL), and NaH (50 mg, 2 mmol), and 3-(bromomethyl)pyridine,3-(chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-bromomethyl-1,3-dimethyl-1H-pyrazole (1 mmol) were added. The mixture was stirred atrt. for 12 h and quenched with H2O (50 mL) in an ice bath. The solutionwas evaporated to remove the THF and extracted with CH2Cl2(2×30 mL). The organic layer was washed with saturated NaHCO3 andbrine, dried over MgSO4, filtered and concentrated. The residue waspurified by column chromatography using petroleum-EtOAc as theeluent to afford about 35 mg of each phenanthridine compound.

According to the analysis of related databases, 873191-23-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Duo-zhi; Yang, Bi-juan; He, Xiao-li; Fan, Shi-rui; Cai, Jie-yun; Jing, Chen-xu; Zhang, Heng; Zhang, Yu; Li, Lin; Hao, Xiao-jiang; Bioorganic Chemistry; vol. 84; (2019); p. 285 – 294;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics