Category: indolines-derivatives

Related Products of 356068-93-4, 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 356068-93-4 as follows.

To a stirred solution of compound 109 (0.2 g, 0.67 mmol) in DMF(30 mL) at O0C was added etaOBt (0.136 g, 1.0 mmol), triethylamine (0.24 mL, 1.67 mmol), ECDI etaC1 (0.192 g, 1.0 mmol) and benzene- 1,2-diamine (0.2 g, 2.0 mmol) successively. The mixture was stirred for 72 h at room temperature, diluted with water (20 mL), brine (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain the product 10 as a yellow solid (0.13 g, 50.03%). LCMS: 391 [M+l]+, 1H NMR (DMSO-J6): delta 4.83 (s, 2eta), 6.58 (t, J= 7.2 Hz, IH), 6.78 (d, IH), 6.84 (m, IH), 6.92 (t, J= 7.8 Hz, 2H), 7.25 (d, IH), 7.74 (m,2H), 9.00 (s, IH), 10.90 (d, IH) ,13.75 (s, IH), 1H NMR (DMSO-D2O) ^ 2.41 (s, 3H),2.44 (s, 3H), 6.62 (t, J= 7.4 Hz, IH), 6.78 (d, IH), 6.89 ( m, IH), 6.95 (m, 2H), 7.19 (d, IH), 7.67 (m, 2H).

According to the analysis of related databases, 356068-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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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. 24566-80-1, name is 2-(10-Bromodecyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(10-Bromodecyl)isoindoline-1,3-dione

Preparation of Compound 2, Sodium Salt; [0049] Into a 3-necked, 250 mL round-bottom flask were measured 9.0 g (131 mmol) sodium nitrate, 15.0 g (14 mmol) of 10-bromodecyl phthalimide and 150 mL DMSO. The reaction mixture was stirred at room temperature for about 20 minutes, at which time 24.36 mL (426 mmol) of glacial acetic acid were added dropwise over 10 minutes. The reaction mixture was stirred and heated to 65 C. for about 2 hours, then cooled to room temperature and stirred overnight. The reaction mixture was poured into 200 mL of ethyl acetate. The organic phase was washed with two 100-mL portions of 0.5 N aqueous sulfuric acid, then was extracted with two 100 mL portions of 2 NaOH. The aqueous phase was cooled to 0 C., then acidified to pH=4 with 2N HCl. The resulting solids were collected by filtration, and recrystallized from ethanol:acetone:water (about 1:1:1).

The synthetic route of 24566-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gschneidner, David; Leone-Bay, Andrea; Wang, Eric; Freeman, John J.; O’Toole, Doris C.; Shields, Lynn; US2003/216589; (2003); A1;,
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Application of 1168150-46-6, A common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, molecular formula is C18H15NO4, 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: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds. 4.1.12.1. Methyl (Z)-3-(((2-((dimethylamino)methyl)benzo[d]oxazol-6-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (A1).Yellow solid. Yield: 42%. Mp: 298.2-301.7 C. 1H NMR (400 MHz,DMSO-d6)delta 12.18 (s, 1H, NH), 10.92 (s, 1H, NH), 7.63e7.54 (m, 3H,ArH), 7.48 (dd, J = 7.7, 1.4 Hz, 2H, ArH), 7.41 (d, J= 1.3 Hz, 1H, ArH),7.18 (dd, J = 8.2, 1.5 Hz, 1H, ArH), 6.67 (d, J= 8.3 Hz, 1H, ArH), 6.41(dd, J= 8.4, 2.4 Hz, 1H, ArH), 6.27 (d, J = 2.4 Hz, 1H, ArH), 5.78 (d,J = 8.2 Hz, 1H, ArH), 4.66 (s, 2H, CH2), 3.76 (s, 3H, OCH3), 2.95 (s, 6H,CH3). 13C NMR (101 MHz, DMSO-d6)delta 170.60, 166.93, 159.24, 156.11,144.40, 136.30, 133.69, 132.77, 132.51, 130.74, 129.86, 129.67, 128.80,123.94, 123.38, 121.84, 117.91, 117.36, 110.33, 109.83, 96.95, 60.48,56.49, 52.21. HRMS (ESI) for C27H24N4O4 [M+H]+, calcd: 469.1870,found: 469.1873.

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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: C13H14BrNO2

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

The synthetic route of N-(5-Bromopentyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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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. 2058-74-4, name is 1-Methylisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 2058-74-4

General procedure: A mixture of 20 mmol of isatine 1a-1f, malononitrile (2), 5,5-dimethylcyclohexane-1,3-dione (3) or 8-hydroxyquinoline (4) and 1 mL of aqueous trimethylamine in 80 mL of ethanol was stirred under reflux for 2 h, after which 40 mL of the solution was distilled off, and the remaining solution was left to stand in the cold. The crystals that formed were filtered off and recrystallized from ethanol.

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; Harutyunyan, A. A.; Pogosyan, M. V.; Pogosyan, S. A.; Russian Journal of Organic Chemistry; vol. 56; 2; (2020); p. 213 – 217; Zh. Org. Khim.; vol. 56; 2; (2020); p. 204 – 209,6;,
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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, Computed Properties of C9H4F3NO3

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
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341988-36-1, name is Methyl indoline-6-carboxylate, 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. name: Methyl indoline-6-carboxylate

A solution of methyl indoline-6-carboxylate ( 0.830 g, 4.68 mmol) in dry tetrahydrofuran ( 20 mL ) was treated at 23 0 C and under nitrogen with lithium aluminum hydride ( 0.23 g, 6.08 mmol) and the resulting mixture was stirred for 3.5 h. The reaction mixture was carefully quenched by successive addition of ethyl acetate ( 1 mL ), water ( 0.2 mL), 15 percent aqueous sodium hydroxide ( 0.2 mL ) and water ( 0.6 mL ). The solid formed was filtered and the filtrate was concentrated under reduced pressure. Chromatography of the residual oil on silica gel ( elution ethyl acetate ) followed by distillation under vacuum ( bulb to bulb distillation, bp 95 – 105 ¡ã C / 0.1 torr, air bath temperature ) gave 0.460 g ( 57 percent yield ) of a clear oil which crystallized to a white solid. HPLC (Method A): 0.132 min. HRMS (ESI) calcd for C9Hi2NO [M+H]+ m/z (0724) 150.0913, found 150.0932. NMR (CDC13, 400 MHz) delta ppm: 7.4 (d, J = 7.4 Hz, 1H), 6.66 (dd, J = 7.4, 1.5 Hz, 1H), 6.63 (br. s, 1H), 4.55 (s, 2H), 3.54 (t, J = 8.4 Hz, 2H), 2.99 (t, J = 8.4 Hz, 2H).

The synthetic route of 341988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BANVILLE, Jacques; (230 pag.)WO2016/134450; (2016); A1;,
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Electric Literature of 897957-06-1, A common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, molecular formula is C9H8BrNO, 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.

To a solution of 6-bromo-1-methyl-1 ,3-diotahydro-iotandol-2-one (226 mg, 1 0 mmol) in DMF (6 0 mL) was added zinc cyanide (117 mg 1 ,0 mmol). Then the reaction mixture was degassed and placed under an argon atmosphere and tetrakiotas(triotaphenylphosphiotane)palladiotaum(0) (115 mg, 0 1 mmol) was added The reaction was then placed at 95 C for 100 minutes, at which time it was cooled to room temperature, and diluted with saturated aqueous sodium bicarbonate and dichloromethane The layers were separated and the aqueous layer was extracted two additional times with dichloromethane The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%) to furnish 1- methyl-2-oxo-2,3-diotahydro-1 H-iotandole-6-carboniotatnle, MS. (ES+) m/z 173 0 (M+H)*

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Reference of 32372-82-0,Some common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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.

Isoindoline hydrochloride (31.1 mg, 0.2 mmol), molybdenum disulfide (4 mg, 0.025 mmol) and a stir bar were placed in a reaction tube. After the inert gas was replaced, 1 ml of DMF was added to seal the reaction tube. . The reaction tube was placed in a 150 C oil bath reaction pot, and the reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration, the filtrate was diluted with 15 mL of water, and extracted with ethyl acetate three times, each time 15 mL; The organic product was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate: petroleum ether = 1:3 (1% triethylamine). Black oil, yield 85%.

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

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Ma Juan; (19 pag.)CN107827817; (2018); A;,
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Electric Literature of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

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

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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