Category: indolines-derivatives

Reference of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-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.

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

Statistics shows that 1-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

Reference Example 23 Synthesis of 2-phenyl-6-chloro-8-methylquinoline-4-carboxylic Acid The above-mentioned compound (1.03 g) was formed from 1.95 g of 5-chloro-7-methylisatin and 2.40 g of acetophenone in the same manner as in Reference Example 1. 1 H-NMR(DMSO-d6), delta: 2.53(s, 3H), 7.55(m, 3H), 7.65(d, 1H), 8.03(d, 1H), 8.25(d, 2H), 8.35(s, 1H), 8.46(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; Mitsui Toatsu Chemicals, Inc.; US5627193; (1997); A;,
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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. 39755-95-8, name is 5-Methoxyisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Methoxyisatin

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
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2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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. Product Details of 2913-97-5

Under a nitrogen atmosphere, to a mixture of NaH (560 mg, 22 mmol) and anhydrous THF (90 mL), a solution of diethyle(2-oxopropyl)phosphonate (4.27 g, 22 mmol) in THF (60 mL) was added over 10 min. The resulting solution was stirred at r.t. for 1 h. Then Compound 2 (6.24 g, 33 mmol) was dissolved in THF (30 mL) and was added dropwise to the above solution. The reaction mixture was stirred at r.t. for a further 3 h. The reaction was quenched with H2O, and THF was removed in vacuo. The residue was then extracted with CH2Cl2 and the combined organic layer was washed with 1N HCl and saturated NaHCO3, dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with Hexane/EtOAc (1:1) to provide Compound 3 (4.6 g, 20 mmol, 60percent) as a white solid. 1H NMR (CDCl3, 400 MHz) delta 7.91 (m, 2H), 7.79 (m, 2H), 6.81-6.74 (m, 1H), 6.16-6.11(dt, J=1.6, 16.0 Hz, 1H), 4.49 (dd, J=1.6, 4.8 Hz, 2H), 2.27 (s, 3H); 13C NMR (CDCl3, 100 MHz): delta 197.7, 167.7, 139.7, 134.4, 131.9, 131.8, 123.7, 123.6, 38.3, 27.2; MS (ESI, positive) m/z calcd. for C13H12NO3 [M+H]+: 230, found: 230.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF DELAWARE; Zhuang, Zhihao; Li, Guorui; (15 pag.)US9605297; (2017); B2;,
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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. 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;,
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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;,
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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;,
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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;,
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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. 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;,
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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;,
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