Month: March 2021

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. 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H5ClF3N

General procedure: To an ice cooled suspension of NaH (3.3mmol) in dry THF (20mL) under nitrogen atmosphere was slowly added a solution of the ketone 8a-e(1mmol) in THF (5mL). The resulting suspension was stirred for 30min at 0C and then a solution of the corresponding trifluoroacetimidoyl chloride 9a-e (1mmol) in dry THF (3mL) was slowly added dropwise at 0C and then further stirred at room temperature for 3h. The resulting orange-brown solution was evaporated under reduced pressure, water was added carefully (20mL) and extracted with CHCl3 (2¡Á20mL). The organic extract was separated, dried over anhydrous magnesium sulfate and evaporated obtaining a brown oil, which was further purified either by recrystallization or column chromatography (silicagel, Hex 7: EtOAc 3).

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romero, Angel H.; Salazar, Jose; Lopez, Simon E.; Journal of Fluorine Chemistry; vol. 169; (2015); p. 32 – 37;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 16799-05-6,Some common heterocyclic compound, 16799-05-6, name is 3-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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 tert-Butyl {9-[2-(3-Chlorophenyl)ethyl]-4-methyl-1-methylthio-carbazol-2-yl}acetate Following a procedure and using relative proportions of starting materials similar to those described in Example 4, but using tert-butyl (4-methyl-1-methylthiocarbazol-2-yl)acetate and 2-(3-chlorophenyl)ethyl bromide as starting materials, the title compound was obtained in a yield of 73% as an oil.

The synthetic route of 16799-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5877199; (1999); A;,
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. 57946-56-2, name is 4-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-2-fluoroaniline

EXAMPLE 5 Preparation of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide A solution of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extract is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a purple oil. Flash column chromatography of the oil using silica gel and 15 to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, 69% yield, mp 81-82 C.) which is identified by 1H, 13C and 19F NMR spectral analyses.

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

Reference:
Patent; American Cyanamid Co.; US6303783; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4152-90-3, 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 4152-90-3 as follows.

To compound 2 (3 g, 9.2 mmol) at room temperatureEthanol (50mL)Et3N (2.6 mL, 18.4 mmol) was added to the solution.And 3-chlorobenzylamine (2.1 mL, 18.4 mmol),The resulting mixture was stirred at 40 ¡ã C for 5 h;Concentrated and the residue is purified by silica gel column(by volume ratio, DCM: MeOH: NH3¡¤H2O=200:10:0.1),Obtaining colorless oily compound 3(3.13g, 82percent),

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Bio-technology Institute; The Chinese People’s Liberation Army Military Academy Of Sciences Military Medical Institute; Liu Mingliang; Lv Kai; Zhong Wu; Cao Ruiyuan; Wang Apeng; Yan Yunzheng; Tao Zeyu; He Qinghao; Wang Hongjian; Li Wei; Geng Yunhe; (29 pag.)CN108892693; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, 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 3972-56-3, category: chlorides-buliding-blocks

General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with NaH (60.0 mg, 60percent,1.2 mmol) and o-xylene (1 mL), and then phenol (1.2 mmol) wasadded. After stirring for 15 min, aryl halide (1.0 mmol) and the solution of Pd(dba)2 (11.5 mg, 0.02 mmol) and L1 (13.7 mg, 0.03 mmol) in o-xylene (1.5 mL) were added sequentially. The septum was replaced with an inside reflux condenser, and then the reaction mixture was stirred for 18 h at 110 C. Then, reaction mixture was cooled to room temperature and quenched with saturated NH4Cl(5 mL). After separating the organic phase, the aqueous phase was extracted with diethyl ether (3 mL3), and the combined organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and then the crude material was purified by column chromatography on silica gel.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhang, Yi; Ni, Gang; Li, Chengjun; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 71; 30; (2015); p. 4927 – 4932;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. Safety of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

The synthetic route of 918538-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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 3,5-dichlorobromobenzene (225 mg, 1 mmol), 4-hydroxypiperidine (101 mg, 1 mmol), BINAP (31.2 mg, 0.05 mmol), and NaOtBu (114 mg, 1.2 mmol) in toluene (3 mL) under argon, was added Pd(OAc)2 (8 mg, 0.03 mmol). The resulting reaction mixture was stirred at 100oC for 4 h. The flask was cooled to room temperature and then partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with brine, and dried over Na2SO4. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (4/1) to afford 1-(3,5-dichlorophenyl)piperidin-4-ol as a colorless oil (210 mg, 85percent) as well as a small amount of 1-(3,5-dichlorophenyl)piperidin-4-one (10 mg, 5percent). A mixture of the above product (210 mg, 0.85 mmol) and Dess-Martin periodinane (424 mg, 1 mmol) were dissolved in DCM (4 mL) and stirred for 1 h at room temperature. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (15/1) to afford 1 as a colorless oil (169 mg, 77percent). 1H NMR (500 MHz, CDCl3) delta 6.82 (d, J = 2.0 Hz, 1H), 6.78 (d, J = 1.5 Hz, 2H), 3.61 (t, J = 6.0Hz, 4H), 2.55 (t, J = 6.0 Hz, 4H); 13C NMR (125 MHz, CDCl3) delta 207.3, 150.7, 136.0X2, 119.1, 113.5X2, 47.7, 40.5; MS (ESI): m/z 244.0 [M+H]+.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yinan; Silverman, Richard B.; Tetrahedron Letters; vol. 54; 6; (2013); p. 573 – 575;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 452-83-5 as follows. Safety of 2-Chloro-5-fluoroaniline

Example 1; Preparation of 6-methoxy-8-[4-(l-(5-fluoro)-qumolin-8-yl-piperidin-4-yI)-piperazin-l- ylj-quinoine (Form A)Step 1: 5-Fluoro-8 chloroquinolineTo a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and wi-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 mL of 70 % sulfuric acid dropwise. The reaction temperature was raised to 140 C for 2 h. The mixture was then cooled, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and extracted with CH2CI2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP = 74-76C; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

According to the analysis of related databases, 452-83-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; WO2007/146116; (2007); A2;,
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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C15H14BrClO

To a solution of aryl bromide 143 (1.50 g, 4.62 mmol) in dry THF (6.2 mE) and dry toluene (24.6 mE) was added dropwise n-butyllithium in n-hexane (1.6 M solution, 5.2 mE, 8.32 mmol) at -78 C. under N2. The reaction mixture was stirred for 30 mm at -78 C. under N2. To this mixture was added triisopropyl borate (1.7 mE, 7.39 mmol) at -78 C. under N2. The temperature of the mixture was allowed to increase to -20 C. over 2 h. To this mixture was added 1M HC1 (aq) (30 mE) at -20 C., and the mixture was stirred at 0 C. for 1 h. The aqueous phase was extracted with EtOAc (4×30 mE) and the combined organic extracts were washed with brine, dried over anhydrous Mg504, and filtered. Concentration of the filtrate followed by flash chromatography (hexane:EtOAc, 2.5:1) yielded aryl boronic acid 124 (684 mg, 51%) as a white solid.

The synthetic route of 461432-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Chinese University of Hong Kong; Shing, Tony Kung Ming; NG, Wai-Lung; LI, Ho Chuen; LAU, Kit-Man; LAU, Clara Bik San; (39 pag.)US2018/127343; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (200 mg, 862 mumol, Eq: 0.95) and 5-(4-isopropylpiperazin-1-yl)pyridin-2-amine (200 mg, 908 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this reaction mixture was added sodium hydride (116 mg, (60% in mineral oil), 2.9 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min then allowed to warm to room temperature and stir 18 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with water and EtOAc. The organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 20% (60:10:1 DCM:MeOH:NH4OH)/DCM gradient) to give a residue that was placed under high vacuum for 18 h to afford (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine (78 mg, 23%). LC/MS-ESI observed [M+H]+ 372.

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, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics