Category: indolines-derivatives

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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 23 Synthesis of 2-methyl-7-[1,2-dihydro-5-methyl-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (IV-4) Similar procedure as Example 20, 5-methylindolin-2-one 0.41 g (2.8 mmol) and 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) 0.5 g (2.6 mmol) were reacted for 13 hours at 80 to 90 C., and 0.39 g (46%) of the titled compound as a yellow solid was obtained. 1H-NMR(500 MHz, DMSO-d6) delta 14.66(s, 1H, -NH-1), 12.03(s, 1H, -COOH), 10.82(s, 1H, -NH-1′), 7.46(s, 1H, H-4′), 6.96(d, 1H, J=7.70 Hz, H-6′), 6.80(d, 1H, J=7.75 Hz, H-7′), 3.10(t, 2H, -CH2-4), 2.93(t, 2H, -CH2-6), 2.53(s, 3H, -CH3-2), 2.32(s, 3H, -CH3-5′), 1.95(m, 2H, -CH2-5); ESI-MS: 323.2 [M+H]+; 321.1 [M-H]-.

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

Reference:
Patent; JIANGSU SIMCERE PHARMACEUTICAL R&D CO., LTD.; US2010/160318; (2010); 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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Reference Example 1 5-Chloroacetyloxindol (45g) was added to 180ml of pyridine and the mixture was stirred at 80C for an hour. After completion of reaction, the mixture was allowed to cool and crystals which precipitated were collected by filtration and washed with acetone. The crystals were then recrystallized from methanol to give 5-alpha-pyridinumacetyloxindolchloride. The compound was added to 600 ml of water containing 12.7 g of sodium hydroxide and stirred at 70-80C for 30 minutes. After completion of reaction, the resultant solution was allowed to cool down and acidified with concentrated hydrochloric acid. Crystals which precipitated were collected by filtration and washed with water. The crystals were then recrystallized from a mixture of dimethylformamide (DMF) and water to give 28 g of 5-carboxyoxindol. m.p.: >300C

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; OTSUKA PHARMACEUTICAL CO., LTD.; EP168003; (1991); B1;,
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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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H8F3NO

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (1.85 g, 9.12 mmol),2-(2-(2-(benzyloxy)ethoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 6d (5.69 g, 10.9 mmol), HATU (5.2 g,13.7 mmol) and diisopropylethylamine (4.52 mL, 27.4 mmol) in DMF (40 mL) wasstirred at room temperature for 2 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken up with EtOAc, washed with a 10% solution of K2003 in water, water, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 220 g, heptane/EtOAc 70/30). The pure fractions were combined and concentrated to dryness to give 2-(2-(2-(benzyloxy)ethoxy)-4-ch lorophenyl )-2-((3-methoxy-5- (methylsulfonyl )phenyl)am ino)-1 -(6-(trifluoromethoxy)indol in-i -yl)ethanone 6e (5.6 g).

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 959235-95-1.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
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Synthetic Route of 90725-50-1, These common heterocyclic compound, 90725-50-1, name is 6-Bromo-3-methylindolin-2-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.

[(2R)-2-(4-Iodophenyl)propyl][(methylethyl)sulfonyl]amine (0.295 g, 0.804 mmol) bis(pinacolate) diboron (0.224 g,0.882 mmol) PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol) and KOAc (0.0.276 g, 2.81 mmol) were combined and heated at 80 C. under nitrogen for 24 h. The mixture was allowed to cool to ambient temperature and 6-bromo-3-methyl-1,3-dihydro-1-indol-2-one (0.0.200 g, 0.885 mmol), PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol)), 2M Na2CO3 (2.0 mL, 5.0 mmol) respectively were added. The resulting mixture was heated and stirred at 80 C. overnight and worked up in a manner analogous to the procedure described in example 3 to provide the final title compound, 6-[4-((1R)-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]-3-methylindolin-2-one, (0.050 g). MS: 387(M+1).

Statistics shows that 6-Bromo-3-methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 90725-50-1.

Reference:
Patent; Bender, David Michael; Forman, Scott Louis; Jones, Winton Dennis; Smith, Daryl Lynn; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225127; (2003); A1;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

Weigh 5-trifluoromethoxyBlush1.0g (0.0043mol),5-chloroindole anhydride 0.9g (0.0045mol) was added to a 100ml three-necked flask containing magnetons.Then add 40 ml of chloroform to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol.Obtaining a pure product yellow solid powder,drying,Weighing 1.12g,The yield was 70.9%.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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. Formula: C10H7NO2

In a sealed tube under argon atmosphere, were introduced compound 4 (0.39g, 2.0mmol), DMF (5mL), triethylamine (1.2mL, 8mmol), palladium diacetate (22.5mg, 0.1mmol), tri(o-tolyl)-phosphine (61mg, 0.2mmol) and N-vinylphthalimide (0.52g, 3mmol). The mixture was stirred at 110C for 5h and then hydrolyzed. The formed solid was solubilized in CH2Cl2, washed with water and brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was recrystallized from toluene to afford 5 as a brown solid (50% yield); mp 236C; 1H NMR (300MHz, DMSO-d6): delta 9.00 (s, 1H), 8.42 (d, J=15Hz, 1H), 7.92 (d, J=9.0Hz, 1H), 7.83-7.82 (m, 2H), 7.80-7.74 (m, 2H), 7.53 (dd, J=9.0, 2.8Hz, 1H), 7.46 (d, J=2.8Hz, 1H), 6.25 (d, J=15Hz, 1H), 3.88 (s, 3H); 13C NMR (75MHz, CD2Cl2): delta 165.2, 162.2, 159.5, 153.6, 145.1, 132.8, 132.1, 130.2, 126.5, 127.4, 123.7, 123.3, 100.6, 95.8, 55.8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Article; Bolteau, Raphael; Caignard, Daniel H.; Delagrange, Philippe; Descamps, Florian; Ettaoussi, Mohamed; Melnyk, Patricia; Yous, Said; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Combine 6-bromo-2, 3-dihydro-isoindol-1-one (0.200 g, 0.94 mmol), bis- pinocalatodiboron (0.264 g, 1.04 mmol), palladium (II) acetate (16 mg, 0.07 mmol) and tricyclohexylphosphine (26 mg, 0.09 mmol) in a 50 mL flask. Add acetonitrile (10 mL) and cesium fluoride (0.428 g, 2.82 mmol); fit flask with condenser and heat in a 90 C oil bath for 1 hour. Cool to room temperature and add trifluoro-methanesulfonic acid 6- methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (0.200 mg, 0.38 mmol), palladium (II) acetate (13 mg, 0.05 mmol) and tricyclohexylphosphine (20 mg, 0.07 mmol), cesium fluoride (0.172 g, 1.13 mmol) and acetonitrile (5 mL). Heat mixture in a 90 C oil bath for 1 hour. Cool reaction to room temperature and filter through celite and wash celite pad with ethyl acetate (60 mL). Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting the material with methanol in dichloromethane (0 to 15%) to give 110 mg of the title compound (57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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Synthetic Route of 199328-10-4, These common heterocyclic compound, 199328-10-4, name is Methyl Oxindole-5-carboxylate, 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.

Step 1: A mixture of compound 1 (200 mg, 1.0 mmol) and HC1 (2.0 M in H20, 5 mL) was heated to 100C for overnight. The mixture was concentrated to get compound 2 (180 mg, 97%) as light yellow solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; VAN DUZER, John, H.; MAZITSCHEK, Ralph; WO2014/121062; (2014); A1;,
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Related Products of 17630-75-0, 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. 17630-75-0, name is 5-Chloro-2-oxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1. 5-Chloroindoline-2-thione. To a solution of 5-chloroindolin-2-one (336 mg, 2 mmol) in toluene (12 ml) was added Lawesson’s Reagent (1.2 g, 3 mmol). The mixture was stirred at 105C for 3 hr. The resulting mixture was cooled and concentrated under reduced pressure. The residue was diluted with water (40 mL) and extracted with DCM (40 mL). Combined organic layers were dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give 5-chloroindoline-2-thione (270 mg, 75% yield) as a white solid. LC-MS: m/z: 184(M+H)+.

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

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
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