Month: August 2021

Application of 14192-26-8, 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. 14192-26-8 name is Methyl 2-oxoindoline-6-carboxylate, 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.

Under the room temperature, 19.1g (100mmol) methyl 2-oxindole-6-carboxylate was suspended in 60 ml toluene. Then add 25.6g (150mmol) chloroacetic anhydride. The mixture at 120 C was heated under reflux for 3 hours, then cooled to 80 C, and in 30 min panega 30 ml methyl cyclohexane, and slowly to room temperature; separating the mother liquor, and with the freezing methanol washing the solid, dry, to obtain white crystal 25.36g, the target compound, the yield is 95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-oxoindoline-6-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Southeast University; Ji, Min; Chen, Hao; Cai, Jin; Liu, Haidong; Li, Rui; (13 pag.)(2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9NO2

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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 7699-18-5.

Reference:
Article; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H16BrNO2

A mixture of the product of Step 1 (1.5 g, 5.0 mmol), allyltributylstannane (2.48 g, 7.5 mmol) and Pd(PPh3)4 (0.58 g, 0.5 mmol) in toluene (20 mL) was stirred at 100 C overnight under a nitrogen atmosphere. The mixture was loaded directly to a silica gel loading cartridge and purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to give the title compound (0.88 g, 68%). 1H NMR (CDC13) delta: 7.76 (br. s, 1H), 7.15 (t, J=7.7 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.88- 5.98 (m, 1H), 5.01-5.11 (m, 2H), 3.93-4.09 (m, 2H), 3.32 (d, J=6.3 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 1.57 (s, 9H).

The synthetic route of 885272-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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 stirred solution of i-2 (448 mg, 3.37 mmol) and i-i (1000 mg, 3.37 mmol) and Potassium carbonate (931 mg, 6.74 mmol) in Acetone (20.0 mL). It was stirred at room temperature for 16 hours. It was diluted with water and extracted with ethyl acetate. Organic part was dried oversodium sulfate, concentrated under reduced pressure and purified by column chromatography using (silica, gradient, 0%-30% ethyl acetate in hexane to afford 3 as off white solid. Yield-20%; LC MS: ES+ 349.3.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; HE, Minsheng; MICHAEL, Ryan, E.; (768 pag.)WO2017/197055; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Computed Properties of C9H9NO2

General procedure: To a stirred solution of oxindole (1a, 67 mg, 0.5 mmol), acetophenone (72 mg, 0.6 mmol), and pyridine (59 mg, 0.75 mmol) in dry THF (0.5 mL) was added dropwise a solution of Ti(OiPr)4 (284 mg, 1.0 mmol) in THF (0.3 mmL), and the reaction mixture was stirred at room temperature for 4 h. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/ether, 2:1) 2e-Z (92 mg, 78%) and 2e-E (18 mg, 15%) were obtained. Other compounds were synthesized similarly, and the structures of known compounds 2a-e and 2k-p were characterized by comparing their melting points and 1H NMR spectrum with the reported.3,4 The selected spectroscopic data of unknown compounds 2f-j and 2q are as follows.

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; Lee, Hyun Ju; Lim, Jin Woo; Yu, Jin; Kim, Jae Nyoung; Tetrahedron Letters; vol. 55; 6; (2014); p. 1183 – 1187;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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 169037-23-4, Product Details of 169037-23-4

Step 1 5-(Trifluoromethoxy)isatin (2.00 g, 8.65 mmol) was dissolved in 1N aqueous sodium hydroxide solution (150 mL) and aqueous hydrogen peroxide (30-35%, 2.45 mL) was added dropwise at room temperature to this solution. The reaction mixture was stirred at room temperature for 20 min., and adjusted to pH 3-4 by adding 1N hydrochloric acid. The precipitated insoluble material was collected by filtration, and washed with water to give 5-(trifluoromethoxy) anthranilic acid as a brown powder (1.88 g, 98%).

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; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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. Application In Synthesis of 5-Nitroindoline

7-Bromo-5-nitroindoline (22A): [0239] Bromine (1.569 mL, 30.5 mmol) was added dropwise to an ice-cold solution of 5-nitro indoline (5 g, 30.5 mmol) in acetic acid (50 mL), and the mixture was stirred for 1 h. Acetic acid was concentrated under reduced pressure, and the resulting solid was triturated with water to afford the title compound (6 g, 80%) as a yellow solid, which was carried on to the next step without further purification. 1H NMR (300 MHz, DMSO-d6): delta 8.07 (d, J=2.1 Hz, 1H), 7.84 (d, J=2.1 Hz, 1H), 7.3 (bs, 1H), 3.7 (t, J=8.7 Hz, 2H), 3.17 (t, J=8.4 Hz, 2H). ESI-MS m/z=243 (M+H)+.

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

Reference:
Patent; GlaxoSmithKline LLC; CHEUNG, Mui; TANGIRALA, Raghuram S.; US2014/148437; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 65435-04-3, 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 65435-04-3 as follows.

A suspension of 9.3 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.

According to the analysis of related databases, 65435-04-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Bromo-1-methylindolin-2-one

To I-3.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R8 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C. for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgSO4 and concentrated. The residue is purified via flash chromatography (cyclohexane/EA=70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

According to the analysis of related databases, 897957-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 350797-56-7, name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, molecular formula is C22H23N3O4, 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: C22H23N3O4

A solution of compound XX (30.0 g) in ethyl acetate (300 ml) was charged to an autoclave and 5% platinum on charcoal (50% wet; 12.0 g) were added. The reaction mass was stirred at 25-30C for 8 to 10 h at a hydrogen pressure of 8-10 bar. The resulting suspension was filtered, and the solvent evaporated to afford 25.0 g of the racemic mixture of compound V.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 350797-56-7, its application will become more common.

Reference:
Patent; SANDOZ AG; KUMAR LUTHRA, Parven; BHUTA, Sachin; ABHINAY, Chandrakant Pise; DATTATRAYA, N., Chavan; SHASHIKANT, D., Metkar; WO2013/56842; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem