Category: indolines-derivatives

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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 argon atmosphere, 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) was dissolved in tetrahydrofuran(5mL). A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6): delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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

Application of 129487-92-9,Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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 mixture of 4-(4-(1,3-thiazol-2-ylcarbonyl)piperazin-1-yl)dihydrofuran-2(3H)-one (2000 mg) and tert-butyl 5-aminoindoline-1-carboxylate (1.999 g) in toluene (40 mL) was added bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct (1.093 g) at room temperature and the mixture was stirred at 70 C. for 1 hr. To the mixture were added THF and sodium sulfate decahydrate (10.994 g) and the mixture was stirred at room temperature overnight. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, methanol/ethyl acetate) to give the title compound (3.67 g). MS: [M+H]+ 516.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-aminoindoline-1-carboxylate, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 1029691-06-2, name is 2-(3-Oxocyclopentyl)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 1029691-06-2, Recommanded Product: 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

Mix (4-trifluoromethoxy-phenyl)-hydrazine hydrochloride (1.5 g, 6.56 mmol) and (+/-)-2-(3-oxo-cyclopentyl)-isoindole-1,3-dione in EtOH (20 mL) and heat to reflux for 14 hours. Concentrate the reaction mixture in vacuo and dilute the residue with Et2O (150 mL). Place the mixture in an ultrasonic bath for 10 min, then filter off a solid. Concentrate the filtrate to give the crude product. Purify the material on silica gel (120 g) using 10-60% EtOAc/hexanes to give 520 mg (22%) of the title compound as a yellow solid. 1H-NMR (DMSO-d6) delta 11.22 (s, 1H), 7.85 (m, 4H), 7.38 (d, 1H, J=8.8 Hz), 7.28 (d, 1H, J=1.3 Hz), 6.96 (dd, 1H, J=8.8, 1.3 Hz), 5.41 (m, 1H), 3.38-3.11 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Synthetic Route of 552330-86-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 552330-86-6 name is 5-Bromoisoindolin-1-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(6-(1-(and 2-)(4-methoxybenzyl)-2H-tetrazol-5-yl)-4?-methyl-5-sulfamoyl-[1,1?-biphenyl]-3-yl)boronic acid (40 mg, 0.083 mmol) and 6-bromoisoindolin-1-one (19.47 mg, 0.092 mmol) was suspended in ethanol (835 mul) and potassium phosphate tribasic (250 mul, 0.250 mmol). The reaction mixture was sparged with N2 for 5 min. 1,1?-bis(di-tert-butylphosphino)ferrocene palladium dichloride (5.44 mg, 8.35 mumol) was added and the reaction mixture microwaved at 110 C. for 90 min. The crude reaction mixture was diluted with EtOAc and water. The aqueous phase was extract with EtOAc (×2), then the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The reaction mixture was purified by reverse phase HPLC on a C18 column and then eluted with 10% to 100% MeCN in water. The major UV active material was lyopholized to provide a white solid that was utilized directly in the deprotection. LC-MS: calculated for C30H26N6O4S 566.2; observed m/e: 467.5 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Application of 954255-04-0,Some common heterocyclic compound, 954255-04-0, name is 5,6-Difluoroindoline, molecular formula is C8H7F2N, 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.

5,6-difluoro-indoline 0.40g (2.58mmol),3,5-dimethoxybromobenzene 0.58 g (2.71 mmol),3% molar amount of Pd(OAc) 2 (17 mg),6% molar amount of P(t-Bu)3.HBF4 (45 mg),Sodium tert-butoxide (0.50 g, 5.16 mmol) was added to 40 mL of toluene.Heating at 110 C for 12 h,filter,The filtrate is depressurized to remove the solvent.Column chromatography (PE: CH2Cl2 = 5:1) gave 0.45 g of white crystals.The yield was 60%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Difluoroindoline, its application will become more common.

Synthetic Route of 41663-84-7,Some common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione, molecular formula is C9H6N2O4, 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.

In the homogeneous mixing of three reaction bottle, under the protection of nitrogen at room temperature by adding 300 mL of dimethylsulfoxide (moisture <500ppm). Then, 150 g of N-methyl-4-nitrophthalimide and 169 g of sodium phenolate were added, Heated to 120 C for 24 hours. Cooled to room temperature, The reaction solution was slowly added to 900 mL of ice water in China, Stirring for 30 minutes, filtering, filter cake with water 150mL * 3 washing, filter cake out to get the product 171g, the yield of 93%, HPLC purity of 98% These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-5-nitroisoindoline-1,3-dione, its application will become more common.

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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 39603-24-2

General procedure: Sulfonated-beta-cyclodextrin (beta-CD-SO3H) (76 mg, 0.06 mmol) was dissolved in water (5 mL) at RT by stirring to get the clear solution in 50 mL round bottom ask. Further, isatin 2 (0.31 mmol) and tryptamine 1a/isotryptamine 1b (0.31 mmol) were added to the solution under constant stirring and mixture was heated at 80 C for 8-12 h. The progress of the reaction was monitored by TLC. After completion of reaction, it was cooled to room temperature, water was added to it. The aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product obtained was puried by column chromatography using chloroform/methanol (99:1) as an eluent furnishing the product. The spectral and analytical data of all the reported products is consistent with the previous (6c,d,f) reports.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Application of 39603-24-2, These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Application of 20870-90-0,Some common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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 oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-2-oxoindoline, its application will become more common.

Electric Literature of 3484-35-3, These common heterocyclic compound, 3484-35-3, name is 5-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: A reaction mixture of compound 19-21 (2.35 mmol),compound 14-18 (2.14 mmol) and 2 drops of piperidine was stirred at RT for 3 h. The precipitate was filtered off and dried. The crude compound was purified by column chromatography using ethyl acetate in dichloromethane (13%) to afford the desired products (4, 22-32).

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.