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. 391-12-8, name is 7-(Trifluoromethyl)isatin, A new synthetic method of this compound is introduced below., Formula: C9H4F3NO2

The above product (163 mg, 0.654 mmol) was dissolved in 3.2 mL of dry dichloromethane, and Dess-Martin periodinane (290 mg, 0.68 mmol) was added to the solution at room temperature. After the reaction mixture was stirred for 30 min at the same temperature, saturated NaHCO3 aqueous solution was added. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 95/5 to 75/25) to obtain the title compound as a white powder (140 mg, 86%).

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; Tokyo Institute of Technology; Kyoto University; EP2123637; (2009); A1;,
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Electric Literature of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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.

40 g of 3-5-[(2R) -2-aminopropyl] -7-cyano-2,3-dihydro-1H-indol-1-yl propylbenzoate (2R, 3R) -tartrate,Acetonitrile 320 ml,20.6 g of anhydrous sodium carbonate, 26.9 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate was added and stirred under reflux for 24 hours.The reaction solution was cooled, filtered, concentrated under reduced pressure, and 400 ml of ethyl acetate and 320 ml of purified water were added to the concentrate, followed by stirring, separating the layers, and concentrating the organic layer under reduced pressure.To the concentrate, 240 ml of ethanol and 10.5 g of L-(+)-tartaric acid were added, stirred at room temperature for 5 hours, filtered and dried under reduced pressure to make 3-7-cyano-5-[(2R) -2- (2- [ 2- (2,2,2-trifluoroethoxy) phenoxy] ethyl amino) propyl] -2,3-dihydro-1H-indol-1-yl propylbenzoate (2R, 3R) -tartrate Obtained 45.1 g. (Yield 79.3%, ee value = 99.97% or more).

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; Ga Pi Bio Co., Ltd.; East F Ti L Co., Ltd.; Jeong Heon-seok; Kim Ryong-guk; (22 pag.)KR2020/4492; (2020); A;,
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Some common heterocyclic compound, 84575-27-9, name is 7-Methoxyindoline-2,3-dione, molecular formula is C9H7NO3, 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. Quality Control of 7-Methoxyindoline-2,3-dione

To a suspension of 7-methoxyindoline-2,3-dione (1.0 g, 5.6 mmol) in AcOH (5.6 mL) was added bromine (0.35 mL, 6.7 mmol) at 0 C. The mixture was allowed to stir at rt for 2 h and was then poured into ice and stirred for 0.5 h. The resulting mixture was filtered and the solids were washed with H2O to afford the title compound as an orange solid (1.3 g, 92%). MS (ESI): mass calcd. for C9H6BrNO3, 256.0; m/z found, 257.6 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 11.22 (s, 1H), 7.48 (d, J=1.7 Hz, 1H), 7.25 (dd, J=1.8, 0.7 Hz, 1H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84575-27-9, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
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Related Products of 3891-07-4, A common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to about 7.26g 38mmol N- (2- hydroxyethyl) phthalimide of THF solution was dropwise added 40mL has dropped to -10 C, contains about 2.28g 57mmol NaH in 15mL THF was added dropwise. After completing -10 C under stirring for 30min. Then 4.2mL containing about 36.2 In THF 15mL mmol 4- chloro-acetoacetate was slowly dropwise added to the above system, a solution of After completion, the reaction system was naturally warmed to room temperature and stirred overnight. Under ice-cooling, ethanol was added 4mL quenched Off the reaction, the reaction solution was slowly poured into 100mL 1mol / L hydrochloric acid and ice, the aqueous phase was extracted with ethyl acetate, The combined organic phase was washed with saturated sodium bicarbonate solution, washed successively with water, dried over anhydrous sodium sulfate, filtered, The solvent was removed rotary evaporation, and the residue was purified by column chromatography to give compound S815.93g, yield 54%

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; JiangsuSimcere Pharmaceutical Company, Ltd; JiangsuSimcere Pharmaceutical Research Co. Ltd.; Chen, Rong; Liu, Fei; Cong, Xin; Feng, Lin; Li, Haidao; Dong, Qingli; (62 pag.)CN102464608; (2016); B;,
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Reference of 5181-35-1, A common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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.

A mixture of 1A (125 mg, 0.34 mmol), K2CO3 (140 mg, 1.02 mmol)and 1B (1.09 g, 2.04 mmol) in dry DMF (2 mL) was stirred at 70 C for 6 h. After cooling to room temperature, the solution was diluted with MeOH (30 mL). The resulting precipitate was collected by centrifugation (5000 rpm, 15 min). The solid thus obtained was dispersed in water, collected by filtration, washed with MeOH and dried in vacuo. These procedures resulted in 185 mg (73.5 %) of 1C as a yellow solid. MALDI-TOF MS (dithranol): m/z calcd for [M+Na+]: 765.72; found: 765.89. Elemental analysis: calcd for C44H30N4O8 (1C): C, 71.15; H, 4.07; N, 7.54. Found: C,71.10; H, 4.19; N, 7.79.

The synthetic route of 5181-35-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshihara, Daisuke; Noguchi, Takao; Tsuchiya, Youichi; Roy, Bappaditya; Yamamoto, Tatsuhiro; Shinkai, Seiji; Chemistry Letters; vol. 44; 6; (2015); p. 812 – 814;,
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Related Products of 39755-95-8,Some common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, molecular formula is C9H7NO3, 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.

One mmol of the compound of the structure represented by the formula (1-3)50% by weight aqueous solution of TBHP (in such an amount that the amount of TBHP is 0.8 mmol)And 1.5 mmol of K3PO4 were addedInto 5 mL of DMSO,At 20 , 500rpm stirring speed reaction 10h,Extraction with dichloromethane,Concentration and silica gel column chromatography (volume ratio of 3:2 dichloromethane / petroleum ether mixture as eluent) to isolate and purify,The compound of the structure shown by Formula (2-3) was obtained(0.39 mmol, 78% yield).

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

Reference:
Patent; Central China Normal University; Jia Fengcheng; Xu Cheng; Zhou Zhiwen; Wu Anxin; (9 pag.)CN107141292; (2017); 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. 71294-03-6, name is 7-Fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 71294-03-6

Example 1 Preparation of 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one Variant A: 7-Fluoro-1,3-dihydro-2H-indol-2-one (100 g) is introduced as initial charge in 600 ml of N,N-dimethylacetamide and cooled to ca. 0 C. with ice/methanol cooling. A solution of potassium hydroxide (43.2 g) and potassium carbonate (143 g) in 600 ml of water is added and the mixture is briefly after-stirred. Then, 2-chloro-4,6-dimethoxy-1,3,5-triazine (140.8 g) is added and in each case 100 ml of water and N,N-dimethylacetamide are used for after-rinsing. The cooling bath is removed, the mixture heats up to ca. 30 C. It is stirred for 18 hours at room temperature. After adding 150 ml of toluene, dilute hydrochloric acid (ca. 700 ml) is used to adjust the pH to 3-4 and at the same time some antifoam (Fluowet PL 80) is added. The solid is filtered off with suction, washed three times with in each case 250 ml of water and twice with in each case 250 ml of heptane and dried in vacuo at 55 C. This gives the title compound as solid in a purity of 96.6% (187.5 g, 95% of theory). LC-MS: M+H=291 (100%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.37 (s, 1H), 7.64 (d, 1H), 6.97 (dt, 1H), 6.86 (dd, 1H), 4.05 (s, 6H).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Karig, Gunter; Ford, Mark James; Siegel, Konrad; US2013/345422; (2013); A1;,
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Synthetic Route of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

A solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (10 ml.) was cooled in an ice-water bath for 5 minutes. Sodium hydride (45 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (2 mL) was added dropwise and the reaction was stirred for 20 minutes before the dropwise addition of iodomethane (0.07 mL, 1.13 mmol, 1.0 equiv.). The reaction mixture was stirred for 30 minutes before warming to 60 C for 24 hours. Additional sodium hydride (23 mg, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) was added followed by iodomethane (0.04 mL, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) and the reaction was stirred for a further 24 hours at 60 C. The reaction was cooled to room temperature and added dropwise to a saturated solution of NH4CI solution and extracted with ethyl acetate three times. The organics were combined, dried over anhydrous MgS04, filtered to remove the solids, and adsorbed onto silica. Purification by column chromatography (0-70% ethyl acetate in cyclohexane) gave methyl 1 -methylindoline-5-carboxylate (61 mg, 0.32 mmol, 28%) as a white solid.

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

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-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 104618-32-8, Safety of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione

EXAMPLE 2: 3- (Phthalimido) -1 , 2 , 3-tetrahydrocarbazole[0035] 4- (Phthalimido) -cyclohexanone from Example 1 is mixed with 1000 mL AcOH. Phenylhydrazine (46 g) was added and the reaction mixture was heated to reflux. After the reaction was completed, the mixture was cooled down to room temperature and filtered. The cake was washed with AcOH and dried to give the product (102g) as a light yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIRAL QUEST, INC.; WEI, Yuan; LI, Tianqiao; CHI, Yongxiang; ZHU, Jingyang; WO2010/78250; (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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Product Details of 7477-63-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

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; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
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