Author: Jessica.F

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

17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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. Computed Properties of C9H6ClNO2

To a stirred suspension of sodium hydride (60% in mineral oil, 2.4 g, 60.0 mmol) in anhydrous ether (170 mL) was added dropwise dimethyl isobutylmalonate (10.0 mL, 53.8 mmol) over 10 min. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 3 h, and was then chilled in an ice-bath. To the stirred cold solution was added N-(chloromethyl)phthalimide (10.1 g, 51.6 mmol) in one portion. The mixture was allowed to warm to room temperature slowly, and was stirred at room temperature for 18 h, followed by refluxing for 1 h. The reaction mixture was cooled to room temperature, and cold 1 N HCl (215 mL) was added. The organic phase was separated, and the aqueous phase was extracted with ether (40 mL). The combined organic phase was washed with brine (40 mL x 2), dried over MgSO4, and then concentrated on a rotary evaporator to dryness. The residue was triturated with hexanes (60 mL). The product was collected by filtration, washed with hexanes (30 mL x 2), and dried in vacuo to afford dimethyl 2-((l,3-dioxoisoindolin-2- yl)methyl)-2-isobutylmalonate as a white solid (15.3 g, yield 85%).1H NMR (CDCl3) delta (ppm) 7.84 (2H, q, J = 2.8 Hz), 7.72 (2H, q, J = 2.8 Hz), 4.30 (2H, s), 3.78 (6H, s), 2.02 (IH, m), 1.80 (2H, d, J = 6.4 Hz), 0.86 (6H, d, J = 6.8 Hz).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

(R)-methyl l-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2- yl)indoline-5-carboxylate (i?)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (44.2 mg, 0.150 mmol, 1 eq), methyl indoline-5-carboxylate (31.9 mg, 0.180 mmol, 1.2 eq), Pd2dba3 (6.9 mg, 0.0075 mmol, 5 mol%), XPhos (10.7 mg, 0.0225 mmol, 15 mol%) and K2C03 (82.9 mg, 0.60 mmol, 4 eq) were dissolved in tBuOH (1.5 mL, 0.1 M) and heated to 100 C for 21 hours. The mixture was filtered through celite, washed with DCM and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-100% EtOAc/hexanes, 18 minute gradient) gave the desired product as a yellow oil (43.4 mg, 0.0997 mmol, 66%). 1H NMR (400 MHz, Chloroform-;/) delta 8.30 (d, J= 8.6 Hz, 1H), 7.89 (dd, J= 8.6, 1.8 Hz, 1H), 7.82 (d, J= 1.3 Hz, 1H), 7.76 (s, 1H), 4.47 (p, J= 8.5 Hz, 1H), 4.32 – 4.19 (m, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 3.18 (t, J= 8.8 Hz, 2H), 2.21 – 2.11 (m, 1H), 2.04 – 1.98 (m, 1H), 1.86 (ddt, J= 16.3, 8.7, 4.4 Hz, 4H), 1.76 – 1.62 (m, 4H), 0.87 (t, J= 7.5 Hz, 3H). 13C NMR (100 MHz, cdcl3) delta 167.22, 163.83, 154.78, 152.04, 148.37, 137.77, 132.00, 130.05, 125.80, 121.94, 115.94, 113.23, 60.15, 58.76, 51.72, 49.52, 29.62, 29.18, 28.13, 27.07, 26.65, 23.36, 23.02, 9.17. LCMS 436.49.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 5332-26-3

A solution of intermediate ACi (2.03 g) in THF (19 mL) was added dropwise at -78C to a solution of LiHMDS (IM in THF; 10.5 mL) in THF (10 mL). The solution was further stirred at -78C stirred for 1 h and treated dropwise with a solution of Lambda/-(bromomethyl)phthalimide (2.6 g) in THF (19 mL). The reaction mixture was further stirred at -78C for 1 h and at rt overnight. The solution was quenched with IN HCl (30 mL) and extracted with EA. The org. layer was washed with water and brine, dried over MgSO4, concentrated under reduced pressure and purified by CC (Hept/EA 1 :1), affording, after crystallization from EA, a beige solid (2.28 g; 66% yield). MS (ESI, m/z): 392.3 [M+H+].

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; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem