Category: indolines-derivatives

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

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

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

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

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

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

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

Application of 1504-06-9, 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. 1504-06-9, name is 3-Methyloxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a Schlenk bottle, add the 2-indolinone compound (29.4 mg, 0.2 mmol) represented by Formula 1a,Copper nitrate (56.1 mg, 0.3 mmol), potassium persulfate (K2S2O8, 81.0 mg, 0.3 mmol) and ethyl acetate (2 mL) shown in formula 2a,Then, the reactor was stirred under the air atmosphere at 25 C.The reaction progress was monitored by TLC until the raw materials disappeared (reaction time was 2h). After the reaction was completed,Ethyl acetate was further added to the reaction solution, the solid residue was removed by filtration, and the solvent was concentrated under reduced pressure.The target product I-1 (90% yield) can be obtained;

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

Reference:
Patent; Yangtze Normal University; Wu Yan; Chen Jinyang; Liu Jialing; Zhong Chuntao; (9 pag.)CN110590639; (2019); A;,
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. 143262-20-8, name is 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid

(1) 7-Indolinecarboxamide To a mixture of 1-(tert-butoxycarbonyl)-7-indolinecarboxylic acid (3.67 g, 13.9 mmol), chloroform (30 mL) and a drop of dimethyl formamide was added dropwise with stirring oxalyl chloride (5.5 mL, 63.0 mmol) over a period of 5 minutes at room temperature. After the addition, the reaction mixture was warmed to 60 C., and stirred at 60 C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and thereto was added toluene (about 100 mL), and the mixture was further concentrated under reduced pressure. To the residue was added tetrahydrofuran (80 mL), and thereto was added with stirring a 29% aqueous ammonia (55 mL) with stirring under ice-cooling. The mixture was warmed to room temperature and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (SiO2, hexane:ethyl acetate=1:2, and then ethyl acetate) to give 7-indolinecarboxamide (2.02 g, yield: 90%). 1H NMR (DMSO-d6) 67; 7.62 (br, 1H), 7.36 (d, 1H, J=8.1 Hz), 7.08 (d, 1H, J=7.0 Hz), 7.00 (br, 1H), 6.61 (s, 1H), 6.46-6.41 (m, 1H), 3.52 (t, 2H, J=8.5 Hz), 2.90 (t, 2H, J=8.5 Hz)

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 143262-20-8.

Reference:
Patent; Masumoto, Shuji; Kitano, Masahumi; Ohashi, Naohito; US2003/105118; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

172078-33-0, name is Indolin-5-ol, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of Indolin-5-ol

Example 40 5-(6-(5-hydroxyindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one 0.15 g (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.37 mmol) 2,3-dihydro-1H-indol-5-ol, 150 muL (0.87 mmol) DI PEA and 0.13 g (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 44 mg (23% of theory) ESI-MS: m/z=491 (M+H)+ Rt (HPLC-MS): 1.33 min (method C)

The synthetic route of 172078-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem