Month: March 2021

Reference of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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 mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (2.5 g, 12.3 mmol), 2- (4-chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (2.47 g, 12.3 mmol), HATU (7 g, 18.5 mmol) and diisopropylethylamine (6.1 mL, 36.9 mmol) in DMF (40 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. The organic layer was separated, washed with water, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc 85/15). The pure fractions were combined and the solvent was concentrated under reduced pressure to give, after crystallization from CHsCN/heptane, 2-(4-chloro-2- methoxyphenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 17c (4.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-(Trifluoromethoxy)indoline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); A1;,
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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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8BrNO

General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.

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:
Article; Zhang, Ji-Quan; Li, Shu-Min; Wu, Chun-Feng; Wang, Xing-Lan; Wu, Ting-Ting; Du, Yao; Yang, Yuan-Yong; Fan, Ling-Ling; Dong, Yong-Xi; Wang, Jian-Ta; Tang, Lei; Catalysis Communications; vol. 138; (2020);,
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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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Methylindolin-2-one

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 mL of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide. The mixture was stirred for 1 hour, diluted with 100 mL 50% acetic acid in water and filtered. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off-white solid.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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Some common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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: 5-(2-Chloroacetyl)indolin-2-one

A suspension of 93 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid. After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid. The combined yield was 97%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65435-04-3, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 19155-24-9, name is 3,3-Dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,3-Dimethylindolin-2-one

3,3-dimethyl-2,3-dihydro-1H-indol-2-one (500 mg, 3.10 mmol) was dissolved in dry CH2CI2 (25 mL). Tetrabutylammonium tribromide (3.74 g, 7.75 mmol) was added portion wise to the solution. The reaction mixture was stirred at rt overnight. Water was added to quench the reaction. After phases separation, the organic layer was dried over Mg504, filtered and the solutionwas concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with Cyclohexane/EtOAc (70:30). Product fractions were collected and evaporated to dryness to afford 5-bromo- 3,3-dimethyl-2,3-dihydro-1 H-indol-2-one Ex.85a (730 mg, 3.04 mmol) as yellow solid. 1H NMR (300 MHz, DMSO-d6, din ppm): 1.24 (s, 6H), 6.79 (d, 1H, J=8.2Hz), 7.32 (dd, 1H, J=8.OHz, J=2.lHz), 7.52 (d, 1H, J=2.lHz), 10.44 (s, 1 H).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
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Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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 solution of 5-fluoropyridine-3-boroniotac acid (CASNo. 872041-86-6, 80mg, 0 57mmol) in 1 ,2-dimethoxyethane (0 7 mL) was added water (0.3 mL) and ethanol (0,2 mL). The solution was then charged with sodium carbonate (60 mg, 0.57mmol), 5-bromo-1-methyl- 1 ,3-dihydro-mdol-2-one (CASNo. 20870-90-0, 132 mg, 0.57 mrnol), and diotachlorobis(triphenylphosphiotane)palladium (II) (CASNo. 13965-03-2, 20.3 mg, 0 029 mmol) The reaction vessel was sealed and is heated by microwave irradiation at 150 C for 10 minutes. The reaction mixture was cooled to room temperature, filtered and concentrated. The resulting residue was partially punfied by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/ 0.1% TFA) Final purification was accomplished via silica gel flash chromatography (methanol-dichloromethane. 0 to 7%) to afford 5-(5-fluoro-pyriotadin-3-yl)-1-methyl-1 3-dihydro-iotandol-2-one; MS. (ES+) m/z 243 (M+Hr; 1H NMR (400 MHz, DMSO-Cf6) delta ppm 3 18 (s, 3 H) 3,64 (s, 2 H), 7 13 (d, J-7.% Hz1 1 H), 7,73 – 7 77 (m, 2 H)1 8.03 (d, J=9 7 Hz, 1 H), 8 53 (d, J=2 7 Hz, 1 H), 8.79 (s, 1 H),

The synthetic route of 20870-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Related Products of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven dried round-bottomed flask, a solution of the squaramide catalyst I (2 mol%) and 1-acetylindolin-3-one 1 (0.4 mmol) in CH2Cl2(1.0 mL) was stirred at r.t. After 5 min, the o-formyl-(E)-beta-nitrostyrene2 (0.48 mmol) was added and the stirring was continued until the complete consumption of the reactants was observed by TLC.Then the crude mixture was purified by flash chromatography on silicagel using a gradient of n-hexane-EtOAc (9:1 to 1:1) to afford the desired product 3.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mahajan, Suruchi; Chauhan, Pankaj; Loh, Charles C. J.; Uzungelis, Server; Raabe, Gerhard; Enders, Dieter; Synthesis; vol. 47; 7; (2015); p. 1024 – 1031;,
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Reference of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.

1-Acetyl-2-formyl-3-hydroxyindole (XIII) [1]. 198 ml (?1.24 mol) of DMF diethyl acetal is added into a suspension of 56 g (0,32 mol) indoxyl XI in 640 ml of benzene and stirred for 1 hour at 20C. The resulting solution is refluxed for 1 hour. Benzene is evaporated in vacuo, with bath temperature less than 60C. After evaporating benzene, the residue is dissolved in ? 4 liters of water and acidified (pH 2-3) by 60 ml of conc. HCl. After 5 min the solid is filtered and washed with water and isopropyl alcohol. 45.5 g (yield 70%) of compound XIII is obtained. Melting point 122-123C (from isopropyl alcohol). IRS, v, cm-1: 1700, 1620, 1580. MS: M+ 203. Founs, % : C 64.73, H 4.50, N 6.90. C11H9NO3. Calc., %: C 65.02, H 4.47, N 6.89. 1H NMR (CDCl3, delta, ppm): 10.24 (1H, br.s, CHO); 2.79 (3H, s, NCOCH3); 7.34-7.91 (4H, m, Ar). UV-Vis, lambdamax, nm (lg epsilon): 230 (4.22), 257 (4.03), 312 (3.95), 356 HM (3.89).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Acetylindolin-3-one, its application will become more common.

Reference:
Patent; Proton OOO; GRANIK, Vladimir Grigorievich; RYABOVA, Svetlana Yurevna; PARSHIN, Valery Aleksandrovich; ALEKSEEVA, Ludmila Mikhaylovna; GRIGORIEV, Nikita Borisovich; EP2738167; (2014); A2;,
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Related Products of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A mixture of isatin 2 (0.8 mmol), malononitrile (1.0 mmol) and Ca(OH)2 (0.8 mmol, 59.2 mg) in 5.0 mL of methanol was stirred at roomtemperature for 10 min followed by the addition of chrysin 1(0.5 mmol), which was stirred under reflux for 8 h. After completion ofthe reaction, as indicated by TLC, the mixture was cooled to roomtemperature and then purified by flash chromatography to afford thecorresponding product 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhang, Wen-Hui; Chen, Shuang; Liu, Xiong-Li; Feng, Ting-Ting; Yang, Wu-De; Zhou, Ying; Bioorganic and Medicinal Chemistry; vol. 27; 22; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-one, belongs to indolines-derivatives 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 16800-68-3, COA of Formula: C10H9NO2

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

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

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
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