Author: Jessica.F

Related Products of 367-22-6, A common heterocyclic compound, 367-22-6, name is 4-Chloro-3-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.

To a cooled (-10 C) suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (13.21 g, 125 mmol) in Et20 (300 mL) was added dropwise TFAA (12.23 mL, 88 mmol). The mixture was allowed to warm to rt overnight. The mixture was diluted with hexane (300 mL) and filtered. The filtrate was washed with ice water, 10%aq NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated to give N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96% yield), as a pale, yellow solid. MS(ESI) m/z: 242.1 (M+H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

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;,
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Synthetic Route of 918538-05-3, These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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.

General procedure: In a 50mL reaction vial, Pd(PPh3)2Cl2 (30mg, 0.042mmol) and NEt3 (121mg, 1.2mmol) were added to a solution of 12 (80mg, 0.424mmol) and 4-trifluoromethoxylphenylboronic acid (90mg, 0.44mmol) in DMF (28.5mL) and H2O (0.5mL). The mixture was stirred at 80C for 4h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, after filtration, the filtrate was evaporated and purified by chromatography (petroleum ether/EtOAc, 20:1) to give the product 13 as a yellow solid (97mg, 78%).

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

Reference:
Article; Xin, Minhang; Zhang, Liandi; Tang, Feng; Tu, Chongxing; Wen, Jun; Zhao, Xinge; Liu, Zhaoyu; Cheng, Lingfei; Shen, Han; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1429 – 1440;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2401-24-3, 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. 2401-24-3, name is 2-Chloro-5-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product.

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, 2-Chloro-5-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Chang, Cai-Zhu; Zhu, Hui; Li, Yue-Sheng; Dong, Zhi-Bing; Chemistry Letters; vol. 46; 5; (2017); p. 641 – 643;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, 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 4863-91-6, Application In Synthesis of 3-Chloro-5-fluoroaniline

To a solution of compound 37.3 (1 eq) in toluene (37 eq) cooled in an ice water bath was added N,N,N’,N’-te¡êramethylethylenediamine (3 eq) and chlorotrimethylsilane (4 eq) the reaction mixture was allowed to come to rt for 30 min. Iodine (1.2 eq) was added portion wise at 10 C. After the addition of iodine was complete the reaction mixture stirred at RT for 3 h followed by diluting with EtOAc and washing with aq a2S204, dried over Na2SC>4 and concentrated in vacuo to afford a residue. To a solution of 3-chloro-5-fluoroaniline (2 eq) in THF (40 eq) was added sodium hydride (60% oil dispersion in mineral oil 3 eq) and stirred at RT for 15 min. Added a solution of the above residue in THF (10 mL) and stirred at RT for 2 h followed by diluting with EtOAc and washing with 5% citric acid, dried over Na2SC>4 and the solvent removed in vacuo. The residue was purified by flash chromatography (10% EtOAc/Hexane to 100% EtOAc) to povide compound 37.4 (48% yield) as a white foam. EIMS (m/z): calcd. for C21H28CIF2N3O3 (M++Na) 466.92, found 466.00.

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:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-05-0, 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 2106-05-0 as follows.

4-Bromo-5-chloro-2-fluoroaniline To a mixture of 5-chloro-2-fluoroaniline (1 equiv.) in acetonitrile (0.5 M) was added N-bromosuccinimide (1 equiv.) at 25 C. The mixture was stirred at 25 C. for 1 h. The mixture was concentrated to a residue, the residue was purified via silica gel chromatography to give 4-bromo-5-chloro-2-fluoroaniline (91%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta ppm: 7.23 (d, J=10.2 Hz, 1H), 6.88 (d, J=8.4 Hz, 1H), 3.92-2.64 (br, 2H).

According to the analysis of related databases, 2106-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
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. 1207625-18-0, name is 3-Chloro-7H-pyrrolo[2,3-c]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H4ClN3

General procedure: To a 15 mL round-bottomed flask were added a stir bar, 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (51 mg, 0.20 mmol), 4-trifluoromethylbenzyl bromide (52 mg, 0.22 mmol), powdered KOH (42 mg, 0.75 mmol) and DMSO (2.0 mL). The resultant mixture was stirred at room temperature for 22.5 hours before diluting with 100 mL EtOAc and washing with water (¡Á3). The organic layer was isolated, dried, filtered, and concentrated to dryness. The crude product was subjected to FCC to give the title compound as a pale-yellow solid (54 mg, 66%). The title compound was prepared in a manner similar to that described in Example 1 using (4-cyclobutyl-2-fluoro-3-methoxyphenyl)boronic acid and 3-chloro-7H-pyrrolo[2,3-c]pyridazine. MS (ESI): mass calcd. for C17H16FN3O, 297.13; m/z found, 298.1 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 12.05 (s, 1H), 8.15 (d, J=2.2, 1H), 7.80 (d, J=3.4, 1H), 7.71 (m, 1H), 7.21 (d, J=8.1, 1H), 6.61 (d, J=3.4, 1H), 3.94 (d, J=1.2, 3H), 2.44-2.35 (m, 2H), 2.25-2.14 (m, 2H), 2.13-2.05 (m, 1H), 1.81 (d, J=7.1, 2H).

According to the analysis of related databases, 1207625-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
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 14862-52-3 as follows. Recommanded Product: 3,5-Dibromochlorobenzene

To a stirred solution of 1,3-dibromo-5-chlorobenzene (600 mg, 2.20 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (455 mg, 2.20 mmol) in 1,4-dioaxane (15 mL) K2CO3 (920 mg, 6.60 mmol) was added and the mixture was degassed with argon for 20 minutes. Pd(PPh3)4 (76 mg, 0.06 mmol) was added to reaction mixture and degassed for another 20 minutes. The reaction mixture was refluxed under stirring for 8 hours and then filtered through celite pad. The filtrate was concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 15% ethyl acetate in petroleum ether to afford the title compound as white solid (300 mg, 50 %).

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cortendo AB; Blass, B. E.; Abou-Gharbia, M. A.; Childers, W. E.; Iyer, P.; Boruwa, J.; (143 pag.)CN105722823; (2016); A;,
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. 63857-00-1, name is N-((2-Chloro-3-((phenylimino)methyl)cyclohex-2-en-1-ylidene)methyl)aniline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C20H20Cl2N2

Example 20 Synthesis of Indotricarbocyclohexen-mu-(chloro) Cyanine Iodide (Compound 20) 20 g of N-ethyl-2,3,3-trimethyl-3[H]indolium iodide, 11.4 g of compound 18, 6.3 g of sodium acetate anhydrous and 400 mL of ethanol are refluxed in a 1000 mL flask for 1 hour. The solution is cooled to room temperature and slowly added to 4 L of diethyl ether. The green precipitate is collected on a fritted glass filter and purified by flash chromatography on silica 60, 200-400 mesh, eluding with a dichloromethane/methanol 9/1 mixture.

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 63857-00-1.

Reference:
Patent; Caputo, Giuseppe; Della Ciana, Leopoldo; US2002/156288; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

General procedure: To a stirred solution of commercially available or known bromoaniline compound (1.0 mmol) inCH2Cl2 (5 mL) and the corresponding propiolic acid (1.3 mmol, 1.3 equiv) was addeddicyclohexyl carbodimide (DCC, 1.3 mmol, 1.3 equiv) at 0 ¡ãC. Then, the temperature wasgradually raised to 25 ¡ãC over 30 min. The mixture was stirred at the same temperature for 12 h,and diluted with EtOAc (50 mL) and sat. aq. NH4Cl (30 mL). The organic layer was separated,dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, hexanes:EtOAc 8:1 or CH2Cl2 only) to affordpropiolamides 4-s, 5-s, 8a-s, 8b-s, and 10-s.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Sunhwa; Shin, Kye Jung; Seo, Jae Hong; Synlett; vol. 26; 16; (2015); p. 2296 – 2300;,
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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

Compound b (8.5 mg, 18.9 mumol) was dissolved in DMF (0.4 mL), 55percent sodium hydride (8.3 mg, 0.189 mmol) was added, and the mixture was stirred at 50 ¡ã C. for 15 min. N- (2-chloroethyl) hexahydro-1 H-azepine hydrochloride (18.7 mg, 94.5 mumol) was added thereto and the mixture was stirred at 50 ¡ã C. for 12 hours. After cooling, reactionTo the mixture was added a saturated aqueous ammonium chloride solution to stop the reaction, and the mixture was extracted with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by thin layer chromatography (chloroform / methanol / ammonia = 90/3/2) to obtain compound c(10.2 mg, 75percent).

According to the analysis of related databases, 26487-67-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANSAI BUNRI SOGOGAKUEN; TOKYO UNIVERSITY OF SCIENCE; HASEGAWA, MAKOTO; MIZUKAMI, TAMIO; TANAKA, MAKOTO; ISAMU, SHIINA; (82 pag.)JP2016/222659; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics