Chlorides-buliding-blocks

A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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. 363-51-9.

Example 60A N-(2-chloro-6-fluorophenyl)-4-methyl-2-(methylthio)pyrimidine-5-carboxamide Example 21A (16.5 g, 90 mmol) was dissolved in a mixture of 358 mL of dioxane and thionyl chloride (7.84 ml, 107 mmol). Four drops of N,N-dimethylformamide were added. The reaction mixture was stirred for 30 minutes at ambient temperature then 2-chloro-6-fluoroaniline (17.41 g, 120 mmol) was added and the reaction mixture was stirred at 100 C. overnight. After cooling to room temperature, the reaction mixture was slowly poured into a 1000 mL separatory funnel containing 400 mL of saturated aqueous sodium bicarbonate and the mixture extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with aqueous sodium bicarbonate (10% wt, 200 mL) and saturated aqueous brine (200 mL), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco, Redi-Sep column, 2-85% ethyl acetate/hexane, linear gradient) yielded the title compound.

The synthetic route of 2-Chloro-6-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Woods, Keith W.; Mastracchio, Anthony; Lai, Chunqiu; Gandhi, Viraj B.; Penning, Thomas D.; US2013/225589; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 56961-77-4

Under a nitrogen atmosphere, and added at 90 will have the N 1 , the N 1 , theN 3 – triphenyl benzene-1,3-diamine (51.7g), 1- bromo-2,3-dichlorobenzene ( 35.0g), Pd-132 (0.6g ), NaOtBu (22.4g) and xylene (350ml) was stirred for 2 hours the flask washeated. The reaction mixture was cooled until room temperature, water and ethyl acetateto carry out a liquid. Then, the use of silica gel column chromatography (eluent:toluene / heptane = 5/5 (volume ratio)) to be purified, thereby obtaining the N 1 -(2,3-dichlorophenyl) -N 1 , the N 3 , the N 3 – triphenyl benzene-1,3-diamine (61.8g).

Statistics shows that 56961-77-4 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-2,3-dichlorobenzene.

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 94-97-3

General procedure: To an oven dried Schlenk tube was added 2-halo-substituted ynamide 1 (0.24 mmol), PdCl2(PPh3)2 (5 mol%), benzotriazole 2 (0.29 mmol), KOtBu (0.48mmol) and dry THF (1 mL). The contents were sealed under nitrogen atmosphere and stirred at 70C (oil bath temperature) overnight. After completion of the reaction as monitored by TLC, the crude reaction mixture was passed through a pad of celite and washed with ethyl acetate (20 mL) and concentrated in vacuum. The residue was then purified by using silica gel column chromatography using hexane-ethyl acetate as the eluent to afford benzosultams 3-14

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, 94-97-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Siva Reddy, Alla; Leela Siva Kumari; Swamy, K.C. Kumara; Tetrahedron; vol. 73; 19; (2017); p. 2766 – 2773;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, 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 54932-72-8, 54932-72-8

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2¡Á20mL) and brine (2¡Á20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%).

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-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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 50 mL round-bottomed flask was sequentially charged with 8 mmol of N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-(piperazin-1-yl). Base) benzamide compound 1, 30 mmol 1,2-bis(2-chloroethoxy)ethane, 10 mmol anhydrous potassium carbonate, and 20 mL N,N-dimethylformamide (DMF). The reaction was stirred overnight at 60 degrees Celsius, extracted with ethyl acetate and dried over anhydrous sodium sulfate.The solvent was removed on a rotary evaporator and the residue was chromatographed on a silica gel column to give the product 4-((4-(2-(2-(2-chloroethoxy)ethoxy)ethyl)piperazin-1-yl)methyl. (amino)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide compound m (yield: 72%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(2-chloroethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; Hefei Zhong Popular Science Ruisheng Bio-pharmaceutical Technology Co., Ltd.; Liu Qingsong; Liu Jing; Wang Qiang; Liu Feiyang; Wang Beilei; Wang Aoli; Wang Wenchao; Hu Chen; Chen Cheng; Zhao Zheng; Wu Hong; Wang Li; (52 pag.)CN104844566; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, Name is 1-Bromo-4-chlorobutane, 6940-78-9, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

50 g of 7-hydroxy-1H-quinolin-2-one and 400 mL of ethanol and 62.7 g of triethylamine were charged into a 1 L three-necked reaction flask and heated to 60 C,Then 159.5 g of 1-bromo-4-chlorobutane was added dropwise,The temperature was raised to 80 C and the reaction was kept at reflux for 2 hours.The reaction was stopped,Cooled to 10 C,Stirred for 1 hour,The crude product was collected by filtration and then recrystallized from 500 ml of methanol. After heating to reflux, the mixture was cooled to room temperature, stirred for 1 hour, filtered, rinsed with cold methanol 50 mL and dried at 60 C under normal pressure to give 72.0 g. G, yield: 92.2%, HPLC purity 99.5% (1: 2.0)

Statistics shows that 1-Bromo-4-chlorobutane is playing an increasingly important role. we look forward to future research findings about 6940-78-9.

Reference:
Patent; SHANDONG CHUANGCHENG PHARMACEUTICAL CO., LTD; Guo, Ming; Ma, Juliang; Liu, Huaizhen; (6 pag.)CN106008337; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, 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 933190-51-3 as follows.

A microwave vial was charged with a mixture of 8-bromo-6- chloroimidazo[l,2-b]pyridazine (0.8 g, 3.44 mmol), isoquinolin-4-ylboronic acid (0.6 g, 1.734 mmol), dioxane (16 mL), tetrakis(triphenylphosphine)palladium(0) (0.100 g, 0.087 mmol), and K3PO4 (2.60 mL, 5.20 mmol) (2.0 M water solution) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 100 C for 4 h in microwave. The reaction mixture was cooled to room temperature, quenched with water, and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3 X 20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2S04, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by BIOTAGE (30-100% EtOAc/ EtOAc/CH2Cl2, 1.2 L, then 50-100%B/ EtOAc/CH2Cl2, B: 10% MeOH/EtOAc/CH2Cl2, 800 mL) to give the product (0.27 g, 55%). XH NMR (400 MHz, CDC13) delta ppm 9.41 (1 H, s), 8.72 (1 H, s), 8.66 (1 H, d, J=4.53 Hz), 8.03-8.17 (1 H, m), 7.90 (1 H, s), 7.71 (3 H, d, J=3.02 Hz), 7.26 (1 H, d, J=4.53 Hz); LC/MS: Rt = 1.35 min. LC/MS (Condition A): 281.13/283.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 933190-51-3, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; LIU, Peiying; BALOG, James Aaron; WO2011/137155; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life. 1996-29-8

In a sealed tube, to a stirred solution of ferf-butyl (3-(2-oxoimidazolidin-1 – yl)bicyclo[1 .1 .1 ]pentan-1 -yl)carbamate (0.25 g, 0.935 mmol, 1 .0 equiv.) in 1 , 4-dioxane (5 mL) was added 1 -bromo-4-chloro-2-fluorobenzene (0.19 g, 0.935 mmol, 1 .0 equiv). The mixture was degassed by purging with argon for 5 minutes. Then Pd2(dba)3 (0.085 g, 0.093 mmol, 0.1 equiv), xanthphos (0.1 g, 0.187 mmol, 0.2 equiv) and Cs2C03 (1 .21 g, 3.74 mmol, 4.0 equiv) were added to the reaction mixture under argon atmosphere, and the sealed tube was capped and the mixture was stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), filtered through a Celite bed, and the Celite bed washed with excess ethyl acetate. The filtrate was concentrated under reduced pressure to afford the crude product, which was purified by silica gel column chromatography (Combiflash) using 50 % Ethyl acetate in hexane as eluent to obtain ferf-butyl 3-(3-(4-chloro-2-fluorophenyl)-2-oxoimidazolidin-1 – yl)bicyclo[1 .1 .1 ]pentan-1 -yl)carbamate (0.17 g, 65% yield) as an off-white solid. LCMS (ES) m/z = 396.1 [M+H] +.

The chemical industry reduces the impact on the environment during synthesis 1996-29-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey Michael; DEMARTINO, Michael P.; EVANS, Karen Anderson; RALPH, Jeffrey M; KALITA, Biswajit; (278 pag.)WO2018/225093; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-11-8,Some common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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 magnetically stirred solution of 2-(4-chlorophenoxy)aniline (95 mg, 0.432 mmol, 76 muL) in CH2Cl2 (1.5 mL) at room temperature was added dropwise propionylchloride (48 mg, 0.518 mmol, 45 muL) followed several minutes later by ethyldiisopropylamine (0.2 mL). The reaction was stirred at room temperature for a further 17 hours, quenched with H2O (10 mL) and partitioned with CH2Cl2 (10 mL). The aqueous layer was extracted with CH2Cl2 (10 mL), and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified over silica gel with 0-50% ethyl acetate in cyclohexane to yield N-[2-(4-chlorophenoxy)phenyl]propanamide (109 mg, 0.395 mmol), Example 14, in 91% yield. LCMS ESI+: 276 [M+H]+, Rt 9.1 min (LCMS 01).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Chlorophenoxy)aniline, its application will become more common.

Reference:
Patent; Bioversys AG; Schneider, Peter; Riedl, Rainer; Tigges, Marcel; Gitzinger, Marc; Pieren, Michel; Levi, Assaf; Sephton, Mark; Schellhorn, Birgit; Zueger, Patrik; Brand, Michael; Gygax, Daniel; Spies, Peter; EP2762134; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

626-43-7, 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 626-43-7 as follows.

Under constant stirring at 0 C, to a solution of 3,5-dichloroaniline (3.24 g, 20 mmol)concentrated hydrochloric acid solution (12 mL)35 wt.% aqueous solution of acetaldehyde (12.8 mL, 80 mmol) was added dropwise. The reaction mixture was stirred at 0 C for 15 minutes and then gradually warmed to 75 C. And reacted at this temperature for 4 hours. The reaction was cooled to room temperature, poured into ice water, 25% aqueous ammonia solution was added dropwise and made alkaline,Extract with dichloromethane three times.The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The crude product was isolated and purified by silica gel column chromatography (ethyl acetate / petroleum ether, 1: 20) to obtain 2.93 g of the compound 1 as a pale yellow solid in a yield of 69%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 626-43-7, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong University of Technology; Centre national de la recherche scientifique (CNRS); LIU, YAN; LIU, XING GUO; HUANG, DA YA; HUANG, MEI JIE; WANG, DE AN; NGUYEN, MICHELLE; ROBERT, ANNIE; MOONEY, BERNARD; (18 pag.)CN105949120; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics