Month: July 2021

Application of 93-50-5, These common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, 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.

Stepl[00173j To a stirred solution of Intermediate 1(0.25 g, 1.22 mmol) in DMA (3 mL) was added 4-chloro-2-methoxyaniline (0.25 g, 1.58 mmol) followed by NaHMDS (1M in THF, 3.66 mL, 3.66 mmol). The reaction was stirred for 20 minutes and then water was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried under vacuum providing Intermediate 12 (361 mg, 91% yield). LC retention time 3.44 mm [A].

The synthetic route of 93-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); A1;,
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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. 14862-52-3, name is 3,5-Dibromochlorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3Br2Cl

To a solution of 1,3-dibromo-5-chlorobenzene (500 mg, 1.85 mmol) in THF (1 ml) was added cyclopropylmagnesium bromide (3698 mul, 0.5M solution in THF, 1.85 mmol) in a sealed tube and the reaction mixture was degassed with argon for 5 min before tetrakis(triphenylphosphine)palladium (0) (107 mg, 0.09 mmol) was added. The resulting solution was heated to 70 C. overnight, cooled to RT and then quenched with sat. NH4Cl solution and extracted with pentane. The organic phases were combined, washed with water and brine, dried over MgSO4 and filtered through a short pad of silica gel to give the desired product (272 mg, 64%) which did not require further purification. 1H NMR (CDCl3, 300 MHz): 7.28 (aptt, J=2.0 Hz, 1H), 7.08 (aptt, J=1.5 Hz, 1H), 6.97 (aptt, J=1.5 Hz, 1H), 1.83 (m, 1H), 1.04-0.97 (m, 2H), 0.72-0.67 (m, 2H).

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; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); A1;,
Chloride – Wikipedia,
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Related Products of 39191-07-6, 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 39191-07-6 as follows.

General procedure: To a solution of 2,6-bis(chloromethyl)pyridine (1 mmol) in anhydrous acetonitrile (10 mL) was added cesium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 5 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (100:1, v/v) to give the title compound as a colorless liquid or a white solid.

According to the analysis of related databases, 39191-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Chlorides – an overview | ScienceDirect Topics

Application of 33406-96-1, These common heterocyclic compound, 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, 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 2-chloro-5-fluorotoluene (5.0 g) in acetic anhydride (40 ml) was added dropwise under ice-cooling concentrated sulfuric acid (40 ml), and then added dropwise a solution of anhydrous chromic acid (9.3 g) in acetic anhydride (40 ml) for 2 hours. The mixture was stirred at the same temperature for 1 hour, poured into ice-water and extracted with diethylether. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in tetrahydrofuran (10 ml). To the mixture were added water (4 ml) and concentrated sulfuric acid (4 ml), and the mixture was stirred at 100 C. for 30 minutes and cooled. The reaction solution was extracted with ethyl acetate. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give the residue, which was subjected to silica gel column chromatography to give 2-chloro-5-fluorobenzaldehyde (1.6 g). The similar reaction was repeated to give 2-chloro-5-fluorobenzaldehyde (1.2 g). In water (55 ml) was dissolved sodium hydroxide (0.78 g), and to the mixture was added acetone (55 ml), and then added dropwise a solution of 2-chloro-5-fluorobenzaldehyde (2.8 g) in acetone (10 ml). The reaction solution was stirred at room temperature for 2 hours, and acetone was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and concentrated under reduced pressure to give 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g). To a solution of 20% sodium ethoxide in ethanol (0.43 g) was added at room temperature diethyl malonate (0.2 g), and then added little by little 4-(2-chloro-5-fluorophenyl)-3-buten-2-one (0.24 g). The mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled, and the solvent was evaporated. The residue was dissolved in water, and the aqueous layer was washed with ethyl acetate and concentrated. To the reside was added 2M sodium hydroxide (0.7 ml), and the mixture was refluxed for 2 hours cooled. To the mixture was added 2.5M sulfuric acid (0.7 ml), and the mixture was refluxed for 15 minutes. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2-chloro-5-fluorophenyl)cyclohexane-1,3-dione (0.17 g) as oil. A solution of 5-(5-chloro-2-fluorophenyl)cyclohexane-1,3-dione (0.17 g) and ammonium acetate (0.16 g) in ethanol (10 ml) was refluxed for 12 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with sodium carbonate solution, water and saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethanol (3.5 ml) and toluene (6 ml). To the mixture were added 3-oxobutylaldehydedimethylacetal (0.21 g) and powdery potassium hydroxide (34 mg), and the mixture was refluxed. To the mixture was added powdery potassium hydroxide (0.07 g) 30 minutes later; powdery potassium hydroxide (0.07 g) and 3-oxobutylaldehydedimethylacetal (17 mg) 1 hour later; and powdery potassium hydroxide (0.07 g) 1.5 hours later. Then, the mixture was stirred at the same temperature for 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was subjected to silica gel column chromatography(ethyl acetate-hexane) to give 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one. To a solution of 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one in ethanol (10 ml) were added aminoguanidine hydrochloride (0.041 g), concentrated hydrochloric acid (0.078 ml) and water (0.078 ml), and the mixture was refluxed for 4 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate, and to the aqueous layer was added sodium hydrogen carbonate solution to make it alkaline. The solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid (1 ml) and concentrated to give crystals, which were recrystallized from ethanol-ethyl acetate to give 7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 170) (0.05 g) as colorless crystals. mp. 268 C. (decomp.). 1H-NMR(DMSO-d6) delta: 2.76-3.05 (1H, m), …

The synthetic route of 33406-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6350749; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, belongs to chlorides-buliding-blocks 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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

To a solution of 2-bromo-4-chloro-l-fluorobenzene (2093 mg, 9.99 mmol) and 4- (trifluoromethyl)-l//-pyrazole (800 mg, 5.88 mmol) in iVW-dimethylacetamide (10 mL) was added Cs2C03(3831 mg, 11.76 mmol). The mixture was heated to 80C for 12 h. LCMS showed the reaction was completed. The mixture was diluted with water (40 mL), extracted with EtOAc (60 mL x 3). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography on silica (100:1-5:1 petroleum ether: EtOAc) to give the title compound. LCMS (ES, m/z): 325.0, 326.9 [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-Bromo-4-fluorochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; DEBENHAM, John, S.; ZHU, Cheng; (64 pag.)WO2020/86416; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6781-98-2, 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. 6781-98-2, name is 2-Chloro-1,3-dimethylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a schlenk tube with a magnetic bar, 6a (40 mg, 6 mol percent), Pd(OAc)2 (5.4 mg, 3 mol percent), and K3PO4 (594 mg, 2.8 mmol) in 5 mL of THF/H2O (5:1) were placed under argon. Aryl chloride (0.8 mmol) was added via syringe and followed by adding phenylboronic acid (1.2 mmol). The resulting mixture was stirred at room temperature for 12 h. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (petroleum ether/EtOAc=100:1) to give the desired product.

The synthetic route of 2-Chloro-1,3-dimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Taoping; Zhao, Xiaoming; Shen, Qilong; Lu, Long; Tetrahedron; vol. 68; 32; (2012); p. 6535 – 6547;,
Chloride – Wikipedia,
Chlorides – 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 933190-51-3

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (2 g, 8.6 mmol) and 5,6-dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0 C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystallized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (2.4 g, 7.85 mmol, 91.2%) as light brown needles. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.26 (br. s., 1H) 7.95 (s, 1H) 7.81 (s, 1H) 7.55 (s, 1H) 7.15 (d, J=7.93 Hz, 1H) 6.58 (d, J=8.31 Hz, 1H) 4.12 (s, 3H) 3.89 (s, 3H); LC/MS: 305.9 [MH]+.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
Chlorides – 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. 627-42-9, name is 2-Methoxyethyl chloride, A new synthetic method of this compound is introduced below., Computed Properties of C3H7ClO

Methyl 4-hydroxy-3-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)acetamido)benzoate (1.0 equiv), anhydrous potassium carbonate (3.0 equiv) and 1-chloro-2-methoxyethane (2.0 equiv) were mixed in DMF, the resulting mixture was stirred overnight at room temperature and concentrated under reduced pressure, and the obtained residue was diluted with EtOAc and washed with sodium bicarbonate, water and brine. An organic layer was collected and dehydrated with anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography, thereby obtaining methyl 4-(2-methoxyethoxy)-3-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)acetamido)benzoate (white solid, 0.10 g, 87.7% yield). 1H-NMR (400 MHz, CDCl3) delta 9.15 (s, 1H), 9.06 (s, 1H), 7.83-7.80 (m, 1H), 7.32 (d, J=8.0 Hz, 2H), 6.94-6.90 (m, 3H), 4.62 (s, 2H), 4.23 (t, J=4.0 Hz, 2H), 3.89 (s, 3H), 3.78 (t, J=4.0 Hz, 2H), 3.44 (s, 3H), 1.71 (s, 2H), 1.34 (s, 6H), 0.70 (s, 9H); 13C-NMR (100 MHz, CDCl3) delta 166.7, 166.4, 154.8, 151.0, 144.0, 127.4, 126.9, 126.6, 123.4, 121.0, 114.0, 110.7, 70.7, 68.4, 67.0, 59.2, 57.0, 52.0, 38.1, 32.3, 31.8, 31.6; HRMS [M+H] calcd [C27H38NO6]: 472.2699, Found: 472.2699; Purity: 100% (as determined by RP-HPLC, method A, tR=27.57 min).

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONGGUK UNIVERSITY GYEONGJU CAMPUS INDUSTRY-ACADEMY COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; Lee, Kyeong; Won, Mi Sun; Ban, Hyun Seung; Kim, Minkyoung; Kim, Bo Kyung; (40 pag.)US2020/31764; (2020); A1;,
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Synthetic Route of 57946-56-2, A common heterocyclic compound, 57946-56-2, name is 4-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

tert-Butyl 4- {[(4-CHLORO-6-METHOXYQUINAZOLIN-7-YL) OXY3METHYL} PIPERIDINE-1- carboxylate (L. OG, 2. 45MMOL), (prepared as described for the starting material in Example 1), and 4-chloro-2-fluoroaniline (0. 33ML, 2. 94MMOL) were stirred in 2-propanol (30ml) and hydrogen chloride (0. 74ML of a 4M solution in dioxane, 2. 94mmol) was added. The mixture was heated at reflux for 4 hours, cooled and filtered. The solid was dissolved in methanol, placed on an ISOLUTE0 SCX column, washed with methanol and then eluted with 7N ammonia in methanol to give 4- (4-CHLORO-2-FLUOROANILINO)-6-METHOXY-7- (PIPERIDIN-4- ylmethoxy) quinazoline (L. OG, 98%) as a white solid. LC-MS (ESI) 417.1 and 419. 1 [MH] + 1H NMR (spectrum): (DMSOd6) 1.47 (m, 2H); 1.93 (d, 2H); 2.13 (m, 1H); 2. 78 (t, 2H); 3.20 (d, 2H); 4.06 (m, 5H); 7.31 (s, 1H); 7.45 (m, 1H); 7.67 (m, 2H); 7.95 (s, 1H); 8.46 (s, 1H); 9.73 (br s, 1H)

The synthetic route of 57946-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/13998; (2005); A1;,
Chloride – Wikipedia,
Chlorides – 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. 2687-12-9, name is Cinnamyl chloride, A new synthetic method of this compound is introduced below., Quality Control of Cinnamyl chloride

General procedure: Aryl, benzyl or allyl halides (1.0mmol), arylboronic acid (1.2mmol), K2CO3 (1.5mmol), C1 (5×10-6 mol%) and H2O (2.0mL) were added into a sealed tube and the mixture was stirred at 60C for a few hours. After the reaction, the aqueous phase was extracted with ethyl acetate for 3 times (3×7mL). Then the combined organic layers were dried over anhydrous Na2SO4, concentrated under vacuum and purified by column chromatography.

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; Luo, Kaixiu; Zhang, Lu; Yang, Rui; Jin, Yi; Lin, Jun; Carbohydrate Polymers; vol. 200; (2018); p. 200 – 210;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics