Month: July 2021

These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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. name: 4-Chloro-3-fluoroaniline

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

The synthetic route of 4-Chloro-3-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3Cl2N3

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).

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 918538-05-3.

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

These common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, 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. HPLC of Formula: C6H5ClFN

Example 4b N-(2′-Chloro-6′-fluoro-phenyl)-4-methylaniline A solution of 3.91 g 2-chloro-6-fluoroaniline in 4 nm of tetrahydrofuran and 35 ml of chlorobenzene is cooled down to -40 to -45 C. At this temperature, 5.09 g of titanium tetrachloride is added to the solution, followed by the addition of 5.0 g of 1-Methoxy-4-methylcyclohexa-1,4-diene. The reaction mixture is allowed to warm up to approx. -35 C. and stirred for 2 hours at this temperature. A solution of 10.18 g of iodine in 20 ml of tetrahydrofuran and 2.3 ml of acetic acid is then added drop-wise to the reaction mixture and the temperature was allowed to warm up to 0 C. The mixture was stirred for 1 hour at 0 C. and 16 hours at 25 C. Then 3.4 g of iodine is added to the reaction mixture and stirring is continued for additional 24 hours at 25 C. The reaction is finally quenched by pouring the reaction mixture onto a mixture of 250 ml of aeq. Sodium bisulfite (38-40%) and 400 ml of saturated aeq. sodium carbonate. The aqueous phase is extracted with ethyl acetate (1*200 ml and 2*100 ml), the ethyl acetate phases are unified and washed with 100 ml of water. The organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to give a yellow viscous liquid. The liquid was dissolved in hexane/t-butyl-methylether and the solution was filtered over silica gel to obtain, after evaporation of the solvent, 4.33 g of crude product. The product can be used directly in the next step. Alternatively, it can be purified e.g. by column chromatography on silica gel with hexane/t-butyl-methylether (9:1) as eluent to yield pure N-(2-Chloro-6′-fluoro-phenyl)-4-methylaniline. 1H-NMR (DMSO-d6, 500 MS, 300K) delta 2.17 (s, 3H, CH3); 6.53 [dd, J=8.5 Hz, JH-F=1.5 Hz, 2H, HC (2) and HC (6)], 6.94 [d, J=8.0 Hz, 2H HC (3) and HC (5)], 7.16 [ddd, J=8.0 Hz, JH-F=6.0 Hz, 1H, HC (4′)], 7.25 [ddd, J=8.0, 1.5 Hz, JH-F=8.0, 1H, HC (5′)]; 7.34 [ddd, J=8.0, 1.5 Hz, JH-F, 1.5, 1H, HC (3′)]; 7.63 (s, 1H, NH). MS (EI) m/z 235 (100, M+), 200 (35, (M-Cl)+), 185 (55)

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

Reference:
Patent; Acemoglu, Murat; Allmendinger, Thomas; Calienni, John Vincent; Cercus, Jacques; Loiseleur, Olivier; Sedelmeier, Gottfried; Xu, David; US2008/249318; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 54932-72-8, 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. 54932-72-8 name is 4-Bromo-1-chloro-2-methylbenzene, 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 mixture of 4-bromo-l-chloro-2-methylbenzene (5.Og, 24.0 mmol), N- bromosuccinimide (4.4 g, 25.0 mmol), and benzoyl peroxide (700 mg, 2.9 mmol) in anhydrous carbon tetrachloride (85 mL) was stirred at reflux for 4 hours. Dichloromethane (50 mL) was added. The mixture was extracted with 1 N NaOH (1 x 150 mL) and brine (1 x 150 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% EtOAc/hexanes), affording 4-bromo-2-(bromomethyl)- 1-chlorobenzene (4.76 g, 70% yield). The product was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-chloro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 174913-12-3, 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. 174913-12-3 name is 1-Bromo-3-chloro-5-methoxybenzene, 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.

Step 2: 1 -Bromo-2,3-dichloro-5-methoxybenzene. To a solution of 1 -bromo-3-chloro-5-methoxybenzene (300 mg, 1 .35 mmol, 1 equiv.) in DMF (5 ml_) was added trichloro-1 ,3,5-triazinane-2,4,6-trione (1 15 mg, 0.49 mmol, 0.36 equiv.) and the reaction was stirred at 50 C for 3 h. The reaction mixture was concentrated and the crude product was purified by column chromatography (Heptane/EtOAc 100 %? 20: 1) to afford the desired product as a white solid (253 mg, 73 %). LCMS [M+H]+ 254; 1 H NMR (400 MHz, CD3CI) delta 7.09 (1 H, d, J = 3.0 Hz), 6.97 (1 H, d, J = 3.0 Hz), 3.77 (3H , s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2533-69-9, A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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 104-11-0, Quality Control of 1-(4-Chlorophenyl)-N-methylmethanamine

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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, 1-(4-Chlorophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 36556-52-2, 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. 36556-52-2, name is 2,3-Dichloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 67 7-[(2,3-dichloro-4-fluorophenyl)amino]-5-{[2-methoxy-4-(piperazin-l – yl)phenyl]amino}pyrido[3,4-d]pyridazin-4-ol EXAMPLE 67A tert-buty ] 4-(4-(7-(2,3-dichloro-4-fluorophenylamino)-4-oxo-3,4-dihydropyrido[3,4- c/|py ndazin-5-ylamino)-3-metho.xyphenyl)piperazine- l -carbox late A mixture of EXAMPLE 24A ( 162 mg, 0.33 mmol), 2,3-dichloro-4- fluorobenzenamine (90 mg, 0.50 mmol), tris(dibenzylideneacetone)dipalladium (3 1 mg, 0.03 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthenexanthene (20 mg, 0.03 mmol) and potassium 2-methylpropan-2-olate (1 12 mg, 1 mmol) in 2-methylpropan-2-ol (2 mL) was degassed with nitrogen twice and stirred in a sealed tube at 130C for 15 hours. After cooling to ambient temperature, the solution was concentrated and the residue was purified by flash chromatography on silica gel eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 630 (M + H+).

The synthetic route of 2,3-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-2-fluoroaniline

Step 1: Synthesis of 1-(2-amino-4-chloro-3-fluorophenyl)-2-chloroethan-1-one (2) To a stirred solution of AlCl3 (10.0 g, 75.01 mmol) and BCl3 (1M in n-hexane) (74 mL, 75.01 mmol) in CH2Cl2 (80 mL) was added 3-chloro-2-fluoroaniline 1 (9.0 g, 6.18 mmol) followed by a solution of chloroacetonitrile (11.6 g, 153.64 mmol) in CH2Cl2 (20 mL) at 0 C. under inert atmosphere. The reaction mixture was allowed to stir at RT for 30 minutes; heated to reflux temperature and maintained for additional 14 h. The reaction mixture was then cooled to 0 C., added aqueous 3N HCl solution (100 mL) and raised the temperature to reflux and stirred for 3 h. After completion of the reaction by TLC, the reaction mixture was cooled RT, diluted with water (50 mL) and extracted with CH2Cl2 (2*150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by triturating with n-pentane to afford compound 2 (4.5 g, 33%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): delta 7.61 (d, J=9.0 Hz, 1H), 7.35 (br s, 2H), 6.72 (d, J=9.0 Hz, 1H), 5.06 (s, 2H).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; Evans, Jillian Frances; US9051320; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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 61881-19-4, Recommanded Product: 2,2,2-Trifluoro-N-phenylacetimidoyl chloride

In a flask with a dry inert atmosphere are introduced 260 ml of anhydrous THF, it is cooled to -78C and 225 ml are added of LDA 2M solution in THF/n-heptane at a rate allowing to maintain the temperature under -65C. After this diethylmethylphosphonate (34.25 g, 0.225 mol) is quickly added dropwise dissolved in 30 ml of THF and it is shaken for 30 minutes at -78C. N-phenyltrifluoroacetymidoyl chloride is then added dropwise (46.7 g, 0.225 mol) dissolved in 40 ml of THF and it is left with shaking in the same conditions for 1 hour. A solution is added of 2,4-difluorobenzaldehyde (33.6 g, 0.236 mol) in 40 ml of THF, the cold bath is removed and the temperature is allowed to rise to ambient temperature. It is left shaking overnight in these conditions. The following morning 450 ml of HCl 2N are added and the shaking continued for 24 hours. The THF is removed in the rotovapor and the resulting aqueous solution is extracted with AcOEt ( 2×200 ml), washed with a solution of 5% NaHCO3 and with a saturated NaCl solution, it is dried with sodium sulphate, filtered and the solvent evaporated with the rotovapor. In this way are obtained 54.6 g of a reddish liquid crude that solidifies. The crude is distilled at a pressure of 35 mbar and a fraction is collected of (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one at 107-14C (43 g, 81%). Melting point : 50-1C IR (KBr, cm-1) : 1717, 1602, 1583, 1277, 1146, 1059, 7061H-RMN (CDCl3) : 6,9 (m, 2H), 7.05 (d, J=16 Hz, 1H), 7,6 (m, 1H), 8.0 (d, J=16Hz, 1H)13C-RMN (CDCl3): 105.1 (t,J=26Hz), 112,6(dd, J=4, 22Hz) , 116.4 (q, J=291Hz), 118.2, 118.5, 131.5 (dd, J=4, 11Hz), 141.5, 162.5 (dd, J=13, 193Hz), 165,7 (dd, J=13, 190Hz), 180 (q, J=36Hz)

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; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1384477; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics