Indolines-derivatives

These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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. Computed Properties of C11H9NO4

General procedure: The DCC (1.2 equiv) was added to the solution of 1 (0.2 mmol), DMAP (0.2 equiv), and appropriate carboxylic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) at 0 C. The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (2 × 10 mL). Then, the CH2Cl2 solution was washed with 5% HCl (3 × 30 mL), saturated NaHCO3 (3 × 30 mL) and saturated NaCl (3 × 30 mL), respectively. Subsequently, the organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. At last, the residue was purified by column chromatography over the silica gel to yield the pure target compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3339-73-9, its application will become more common.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Guo, Rui-Hua; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2877 – 2888;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-15-4, name is 4,6-Dichloroisatin, 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 18711-15-4, COA of Formula: C8H3Cl2NO2

(1) 1-Methyl-4,6-dichloroisatin A mixture of 60% NaH (20.5 mg), 4,6-dichloroisatin (947 mg), and iodomethane (0.328 mL) in THF (20 mL) were stirred overnight at room temperature, poured into 1 N hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with sat. aqueous NaCl, dried over MgSO4, and concentrated. The residue was washed with hexane to give the title compound (849 mg, 84%). 1H-NMR (DMSO-d6, 300 MHz) delta 3.12-3.11 (3H, m), 7.33-7.30 (2H, m).

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; Sumitomo Pharmaceuticals Co., Ltd.; US6576656; (2003); B1;,
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. 25369-33-9, name is 7-Chloroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Chloroindolin-2-one

Example 54Preparation of 7-chloro-5-[Y2-((‘l S,2S)-2-[l-(5-chloropyrimidin-2-yl)piperidin-4- yli cvclopropyU ethvDaminol -1.3 -dihvdro-2H-indol-2-oneStep 1 ; 7-chloro-5-nitro-13-dihvdro-2H-indol-2-one7-chloro-1,3-dihydro-2H-indol-2-one (8.Og, 47.7 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x)? and dissolved into EtOAc (1 L). This mixture was filtered, washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

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 25369-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6872-06-6, A common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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 7Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(phenylsulfonyl)indolineReagents MW Reagent/raw material (g/mole) Quantity moles 2-methylindoline 133.20 1 g 7.5 mmol benzenesulfonyl chloride 176.62 1.98 g 11 mmol 2-methyl-1- 273.35 0.76 g 2.77 mmol (phenylsulfonyl)indoline 2,3- 234.66 0.5 g 2.13 mmol dihydrobenzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 0.369 g 2.77 mmol Step 1: 2-methylindoline was dissolved in 5 mL dry pyridine, and benzenesulfonyl chloride was dropped in. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When complete as determined by HPLC using the protocol in Example 1 above, as well as by LCMS, the crude reaction was poured into 100 mL cold 1M KHSO4, and extracted twice with 50 mL CH2Cl2. The organic phase was dried, evaporated and purified by CombiFlash to provide 2 grams of 100% pure product (97% yield).

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; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, 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: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

Statistics shows that Isoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 480-91-1.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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-Nitroindolin-2-one

A. A suspension of 5-nitroindolin-2-one (2.0 g, 11.13 mmol), and 10% palladium on carbon (500 mg) in methanol (100 mL) was hydrogenated for 2 hours under 45 psi. The reaction mixture was filtered through celite and the resulting cake was washed with methanol. The filtrate was concentrated to afford 5-aminoindolin-2-one as a tan-colored solid (1.6 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; Schering Aktiengesellschaft; US2005/90541; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, name is 6-Bromoindolin-2-one, 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. Safety of 6-Bromoindolin-2-one

NaHC03 (23 g, 283 mmol, 2.0 eq) and di-tert-butyl dicarbonate (46 mL, 212 mmol, 1.5 eq) were added to a stirred solution of 6-bromoindolin-2-one (30 g, 141.5 mmol, 1.0 eq) in THF (300 mL) at rt. The mixture was refluxed for 3 h, then cooled to rt, diluted with water (100 mL) and extracted with EtOAc (2x 100 mL). The combined organic layers were washed with brine (50 mL), dried and evaporated under reduced pressure. The raw product was purified by column chromatography [silica gel 100-200 mesh, PE/EtOAc = 9:1]. White solid. Yield: 35 g, (79%). 1H NMR (400 MHz, CDCI3, delta ppm): 8.03 (d, J = 1.2 Hz, 1H), 7.27 (dd, J = 8.0, 1.6 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 3.58 (s, 2H), 1.64 (s, 9H).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (168 pag.)WO2017/108204; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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. Computed Properties of C8H4ClNO2

Example 109 2-(6-Chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid thiazol-2-ylamide A mixture of sodium hydride (60% in oil, 264 mg) in N,N-dimethylformamide at 0 C. was treated with a solution of 6-chloro-1H-indole-2,3-dione (1.0 g) in N,N-dimethyl formamide (total volume is 25 mL). The reaction mixture was then stirred for 30 min at 0 C. After this time, the reaction mixture was treated with 2-bromo-4-methyl-pentanoic acid methyl ester (prepared as in Example 9, 1.38 g) and stirred for another 1 h at 0 C. The reaction mixture was then allowed to warm to room temperature and stirred for 3 h. After this time, the reaction was diluted with water and extracted with methylene chloride. The organic layers were combined and then dried over sodium sulfate, filtered to remove the drying agent and the filterate concentrated in vacuo. The residue obtained was then purified by silica gel column chromatography to afford 2-(6-chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-4-methyl-pentanoic acid methyl ester (1.3 g, 76%).

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

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem