Indolines-derivatives

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.

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.

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.

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.

Synthetic Route of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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.

4,7-Dichloroisotin (4.26 g, 19.7 mmol, 1 equiv, Alfa Aesar lot 10173559) and MeOH (70 mL, 16.4 vol) were charged to a 250-mL, three-neck, round-bottom flask equipped with nitrogen line, overhead mechanical stirrer, and a temperature probe. Diethylamine (0.43 g, 0.30 equiv, Sigma- Aldrich lot SHBD5313V) was added over 1 min via syringe (the slurry becomes dark red). l-[4-(Methylamino)phenyl]ethanone 3 (11.4 g, 3.9 equiv, Sigma- Aldrich lot 01129HHV) was added in portions via a plastic funnel, over 15 min. The funnel was rinsed with MeOH (2 x 15 mL, 7.0 vol). The reaction was stirred at ambient temperature (approximately 18-20 C) and periodically sampled for in-process control (IPC) by HPLC. After 40 h of reaction, additional diethylamine was charged to the reaction via syringe (0.16 g, 0.11 equiv) and the stirring continued at ambient temperature. After 64 h, a light slurry formed. Additional diethylamine was charged to the reaction via syringe (0.13 g, 0.09 equiv) and the stirring continued at ambient temperature. After 92 h of reaction IPC by HPLC analysis showed 2.1% AUC of isatin 1 present in the reaction mixture. Additional diethylamine was charged to the reaction via syringe (0.07 g, 0.05 equiv) for a total of 0.55 equiv of base and the stirring continued at ambient temperature over the weekend. After a total of seven days, the reaction was concentrated under reduced pressure (water bath <40 C), the solid residue was dissolved in a mixture of dichloromethane (450 mL) and MeOH (50 mL) at 30 C, and adsorbed over 20 g of silica gel. Purification was carried out in a Combiflash CompanionTM XL system with a RediSep disposable flash 220 g silica gel column (catalog 69-2203-422). Elution of the residual starting material 3 was accomplished with dichloromethane (approximately 20 column vol, while the product TK- 202 was eluted with 10% methanol in dichloromethane. The product containing fractions, where product had already started to precipitate, were combined in two different lots and partially concentrated under reduced pressure. The resulting slurries were filtered and the solid cakes were washed with MeOH to afford two fractions that were dried under high vacuum at ambient temperature for 24 h, then 50 C for 24 h, to afford lot BIO-W-30-17 and lot BIO-W-30-18. The filtrate from both crystallizations were combined and subjected to a second chromatographic purification (on a 40-g RediSep Gold column, catalog 69- 2203-347) using a gradient from dichloromethane to 5% methanol in dichloromethane for elution. The product containing fractions (purity higher than 99% AUC by HPLC) were combined and the product was allowed to precipitate over 2 h. The solid was filtered off, washed with methanol, and dried under high vacuum for 24 h at 50 C to afford lot BIOW- 30-19. A second set of fractions containing product of approximately 95% AUC purity by HPLC were combined, the solid was filtered off, re-dissolved in dichloromethane, and added 20% methanol to precipitate overnight. The precipitated TK-202 was filtered and washed with methanol, then dried under high vacuum for 24 h at 50 C to afford lot BIO-W-30-16. The total combined weight of 5.99 g corresponds to 83% yield of compound. Solid is off- white (with a very pale peach to tan shade). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 603-62-3, name is 3-Nitrophthalimide, 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 603-62-3, Recommanded Product: 3-Nitrophthalimide

Step 1) Synthesis of 2-carbamoyl-6-nitrobenzoic acid This moiety was synthesized using the following protocol. To a solution of potassium hydroxide (6.44 g, 114.4 mmol) in water (200 mL), was added 3-nitrophalimide (10; 10 g, 52 mmol) in portions at 0 C. The suspension was stirred at 0 C. for 3 hours, and then heated to 30 C. for 3 hours. To the solution, was added HCl (40 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hour. The suspension was filtered and washed with cooled water (2*20 mL) to give 2-carbamoyl-6-nitrobenzoic acid (11; 8.5 g, 77%) as a white 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, 3-Nitrophthalimide, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Computed Properties of C9H7NO3

2-Oxo-2,3-dihydro-lH-indole-5-carboxylic acid (7 g, 39 mmol) is dissolved together with benzylalcohol (4.2 mL, 39 mmol) and 4-lambda/,lambda/-dimethylaminopyridine (1 g, 7.9 mmol) in 70 mL DCM and cooled in the ice bath. Then l-ethyl-3-(3-dimethylaminopropyl)carbo- diimide (8.3 g, 43 mmol) is added and the mixture is heated to RT for 12 h. After evaporation of the solvent the residue is taken up in a little methanol and combined with 1 N hydrochloric acid (200 mL). The precipitate formed is filtered and dried. Yield: 6.9 g (65 %) (A86).

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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Application In Synthesis of 2-Oxoindoline-5-carboxylic Acid

Example 2Step 1 :Synthesis of 2-oxo-/V-[(1 R)-1 -phenylpropyl]indoline-5-carboxamideA mixture of 2-oxoindoline-5-carboxylic acid (300 mg, 1 .69 mmol), (1 R)-1 – phenylpropan-1 -amine (228 mg, 1 .88 mmol), HATU (740 mg), 0.16 mL DIPEA in dry DMF (7 mL) was stirred overnight, then concentrated under reduced pressure. The resulting residue was diluted with AcOEt and washed with a saturated aq. solution of K2CO3. The organic layer was dried and concentrated in vacuo. Purification by flash chromatography (Kieselgel, CHCl3:MeOH 15:1 ) provided intermediate 2-oxo-/V-[(1 R)-1 -phenylpropyl]indoline-5-carboxamide: (340 mg, 68%):NMR (300 MHz, DMSO-c/6) delta ppm: 10.59 (s,1H), 8.53 (d,1H), 7.78 (s,1H), 7.76 (d,1H), 7.33 (etaeta,4Eta), 7.22 (t,1H), 6.85 (d,1H), 4.85 (etaeta,1Eta), 3.53 (s,2H), 1.79 (etaeta,2Eta), 0.89 (t,3H); tR: 3.09 min; MS (ESI): m/z (M+H)+ 295; (M+HV293.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102359-00-2, its application will become more common.

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. 15861-23-1, name is Indoline-5-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H8N2

General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.

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.

Some common heterocyclic compound, 71294-07-0, name is 5,6-Difluoroindolin-2-one, molecular formula is C8H5F2NO, 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. Recommanded Product: 71294-07-0

General procedure: A mixture of 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 71294-07-0, its application will become more common.