Category: indolines-derivatives

These common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)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. Computed Properties of C14H16BrNO2

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The synthetic route of N-(6-Bromohexyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
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These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-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. Formula: C8H6N2O3

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

The synthetic route of 5-Nitroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Pharmacia Corporation; US2003/216410; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;; ; Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, SDS of cas: 32692-19-6

Reference Example 98To 5-nitroindoline (1.Og, 6. lmmol) in acetone (12ml), powdered potassium hydroxide (1.7g, 30.5mmol, 5eq) was added followed by the addition of methyl iodide (1.2g, 9. lmmol, 1.5eq) at 00C. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and water was added and the compound was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to yield l-methyl-5 -nitro-2,3-dihydro-l H-indole (l.Og, 92%). The crude compound was used in the next stage without purification. Reference Example 103 l-Methyl-2,3-dihydro-lH-indol-5-ylamine a) Preparation of l-methyl-5-nitro-2,3-dihydro-lH-indoleTo a solution of 5-nitro-2,3-dihydro-lH-indole (Ig, 6.09mmol) in acetone (12ml) was added powdered potassium hydroxide (1.7g, 30.45mmol), followed by methyl iodide (1.2g, 9.14mmol) and stirred overnight at ambient temperature. The solvent was evaporated under vacuum to give a residue, to which water was added and the product extracted with ethyl acetate. Drying and concentration of the organic layer yielded 1- methyl-5-nitro-2,3-dihydro-lH-indole (Ig, 92%) as solid.

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

Reference:
Patent; F2G LTD; WO2006/123145; (2006); A1;,
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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 60434-13-1 as follows. Product Details of 60434-13-1

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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Adding a certain compound to certain chemical reactions, such as: 41663-84-7, name is 2-Methyl-5-nitroisoindoline-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 41663-84-7, HPLC of Formula: C9H6N2O4

EXAMPLE I In a 500 ml three-necked flask equipped with a mechanical stirrer, Dean-Stark trap/condenser, nitrogen inlet, and thermometer was added 25.71 grams (0.20 moles) of p-chlorophenol, 100 ml dimethylsulfoxide, and 150 ml of chlorobenzene. After stirring and nitrogen purging the mixture for 30 min., 15.80 grams of aqueous sodium hydroxide (50.62 wt. %; 0.20 moles) was added. The mixture was heated up to 150 C. with the azeotropic removal of the water of reaction. After the removal of water was complete the temperature was lowered to 60 C. and 41.23 grams (0.20 moles) of 4-nitro-N-methyl phthalimide was added. The mixture was stirred overnight. Upon cooling to room temperature the product precipitated from solution. Filtration, washing the precipitate with water, and recrystallization from isopropanol yielded 50.8 grams of 4-(p-chlorophenyl)-N-methyl phthalimide. The melting point was 131-132 C.

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-Methyl-5-nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; General Electric Company; US4623732; (1986); A;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 32372-82-0, name is Isoindoline hydrochloride, 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 32372-82-0, Recommanded Product: 32372-82-0

The isoindoline hydrochloride (31.1mg, 0.2mmol),Manganese chloride tetrahydrate (5.9 mg, 0.03 mmol),And a stirrer in the reaction tube,After replacing inert gas,Add 1 ml DMF,Seal the reaction tube.Place the reaction tube in a 150C oil bath reaction pot.Stir the reaction for 10 hours;After cooling to room temperature,Diluted with 15mL water,And extracted three times with ethyl acetate,15mL each time;Combine the extracts,Dry with anhydrous sodium sulfate.After filtration, the filtrate was concentrated under reduced pressure.With ethyl acetate:The crude product was subjected to column chromatography with petroleum ether=1:3 (containing 1% triethylamine) as eluent to obtain a pure product.Black oil, yield 81%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Zhang Jingyu; (19 pag.)CN107986927; (2018); A;,
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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. 1201923-48-9, name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate

To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro- 2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 mL) at RT was added 4M HCI in dioxane (56 mL, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 mL) affording the title compound (7.8 g, 99%) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1201923-48-9.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/158372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, 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 317-20-4 as follows.

To a stirring solution of7-fluoroindoline-2,3-dione (12.22 g, 74 mmol) inTHF (40 mL) at 0 oc was added phenylmagnesium bromide (148 mL, 148 mmol)dropwise. The reaction mixture was allowed to stir at room temperature after addition20 was completed. The reaction mixture was judged complete by HPLC after 15 min. Thereaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. Thecombined extracts were washed with brine, dried (Na2S04), filtered and concentrated.The residue was purified by silica gel chromatography (EtOAc/hexane) to affordIntermediate A11A(18.84 g, 88%) as yellow solid: HPLC: RT= 1.810 min (H20/MeOH25 with TF A, CHROMOLITH SpeedROD, 4.6x50mm, gradient= 4 min, wavelength=220 nm); MS(ES): m/z = 226 [M+H+-H20]; 1H NMR (400 MHz, DMSO-d6) 8 10.92 (s,lH), 7.37-7.25 (m, 5H), 7.19 (ddd,J=l0.4, 8.1, 1.3 Hz, lH), 7.04-6.92 (m, 2H).

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GAVAI, Ashvinikumar V.; ZHAO, Yufen; O’MALLEY, Daniel; QUESNELLE, Claude A.; FINK, Brian E.; NORRIS, Derek J.; HAN, Wen-Ching; DELUCCA, George V.; WO2014/47374; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3676-85-5, name is 5-Aminoisoindoline-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. category: indolines-derivatives

Example 112 N-(3-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (182 mg, 0.66 mmol, 1.2 eq) and triethylamine (67 mg, 0.66 mmol, 1.2 eq) were added to a solution of 3-nitrophenylacetic acid (100 mg, 0.55 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (89 mg, 0.55 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 3 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with chloroform/methanol to give a nitro compound (45 mg, 24.1%) containing a minor amount of 4-aminophthalimide as the starting compound. DMF was added to the nitro compound (containing the starting compound, 40 mg, 0.12 mmol). Palladium hydroxide (one small spatula) was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure to give the title compound as a crystal (16 mg, 44.4%). MS m/z: 310 1H-NMR delta: 4.17 (2H, d, J = 5.37 Hz), 5.03 (2H, s),6.38 (1H, s), 6.44 (2H, d, J = 7.81 Hz), 6.51 (1H, s), 6.79 (1H, dd, J = 1.95, 8.05 Hz), 6.96 (1H, t, J = 7.68 Hz), 7.60 (1H, dd, J = 1.71, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 7.74 (1H, s), 8.03 (1H, d, J = 1.95 Hz), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 141452-01-9, These common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, 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.

In the dried Schrank tube, raw porphyrin (0.15 mmol, 32.8 mg), p-toluenesulfonamide (0.3 mmol, 51.1 mg),Iodobenzene acetate (0.15 mmol, 48.3 mg), pentamethylcyclopentadienylphosphonium dichloride (5 mmol%, 4.6 mg), silver triflate (20 mmol%, 7.7 mg),Silver acetate (20 mmol%, 5.1 mg), acetic acid (0.45 mmol, 27 mg)1.5 mL of 1,2-dichloroethane, and the above-mentioned Schalke tube was placed in a 100 o C oil bath.Stir for about 16 h. Stop the reaction and use 2 mLSaturated ammonium chloride is easy to quench the reaction solution.After further extraction with ethyl acetate (4 mL × 5), the organic phases were combined.The solvent was removed on a rotary evaporator. At last,Separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1: 5),Methyl 1-acetyl-7-((4-methylphenyl)sulfonylamino)indoline-5-carboxylate3i (26.1 mg, isolated yield: 45%),This compound was a pale yellow solid.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changzhou University; Sun Song; Dong Yaqun; Cheng Jiang; Yu Jintao; (13 pag.)CN110218172; (2019); A;,
Indoline – Wikipedia,
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