Month: February 2021

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

Electric Literature of 1716-42-3, A common heterocyclic compound, 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, molecular formula is C9H10ClFO, 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.

Example B13; A mixture of l-(3-chloropropoxy)-4-fluoro- benzene (0.025 mol), compound 23 (0.02 mol) and sodium carbonate (0.06 mol) in DMF (150ml) was stirred at 60¡ãC for 12h. The mixture was cooled, poured into ice water, acidified with HC1 and neutralized with NH3. The precipitate was filtered off and crystallized from MeOH. The precipitate was filtered off and dried at 60¡ãC. The residue (2.1g) was converted into the hydrochloric acid salt (1:1) in 2-propanol. The precipitate was filtered off and washed with 2-propanol and DIPE. The residue was dried at room temperature, yielding 1.2g (14.4percent) of compound 13, melting point 227.6¡ãC.

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; JANSSEN PHARMACEUTICA N.V.; WO2006/3147; (2006); 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. 18487-39-3, name is 2,3,5-Trichloroaniline, A new synthetic method of this compound is introduced below., COA of Formula: C6H4Cl3N

EXAMPLE 11 The procedure of the preceding example is followed, except for the following conditions: A 4 N aqueous solution of HCl (120 cc), 2,3,5-trichloroaniline (0.354 g), a palladium-based catalyst (palladium on carbon activated containing 10% of palladium) (0.140 g) and potassium iodide (0.011 g) are introduced. The autoclave is heated at 160 C. for 160 minutes under a total pressure of 18 bars, the hydrogen pressure being 13 bars. The conversion is complete and 3,5-dichloraniline is obtained with a yield of 96.8%.

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; Rhone-Poulenc Agrochimie; US4351959; (1982); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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. Recommanded Product: 210532-25-5

To a suspension of 3-[2-(l,3-dioxo-l,3-dihydro-isoindol-2-ylmethyl)-benzoylamino]-6,6- dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester hydrochloride (1.24 g, 2.4 mmol) in dry dichloromethane (30 mL) was added N,N- diisopropylethylamine (1.67 mL, 9.6 mmol) and 3,5-difluorobenzenesulfonyl chloride (0.77 g, 3.6 mmol). After stirring at room temperature for 3 hours the mixture was diluted with dichloromethane (50 mL), washed with IN HCl, water, saturated solution of NaHCC>3, brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel eluting with ethyl acetate and then with dichloromethane/methanol 98:2 affording the title compound as white solid (1.4 g).IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 10.61 (bs, IH), 7.83 (m, 4H), 7.69-7.63 (m, 4H), 7.56-7.45 (m, 2H), 7.39 (m, IH), 5.05 (s, 2H), 4.72 (bs, 2H), 4.41 (q, J=7.1 Hz, 2H), 1.67 (s, 6H), 1.34 (t, J=7.1 Hz, 3H).

The synthetic route of 3,5-Difluorobenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics