Category: 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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H7NO3

To a suspension of D23 (6.14 g, 35 [MMOL)] in dry tetrahydrofuran (25 mL) was added dropwise BH3-THF (100 mL, 1M in tetrahydrofuran) then heated at reflux overnight. The mixture was cooled to [0C] then quenched by dropwise addition of methanol (10 mL). After stirring at room temperature for 20 minutes 5M HCI (10 [ML)] was added and the mixture heated at reflux for 1 hour. The mixture was cooled to room temperature, the pH adjusted to pH 10 by the addition of 2M [NAOH] (58 mL) and extracted with dichloromethane. The organic layer was dried [(MGS04),] and evaporated. Purification by SCX followed by evaporation gave the title compound D24 as an oil (1.76 g). [MH+] 150.’H NMR [8] (CDCI3) 3.80 (3H, s), 4.17 (2H, s), 4.20 (2H, s), 6.75-6. 83 (2H, m), 7.13 [(1H,] d).

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.

Adding a certain compound to certain chemical reactions, such as: 84378-94-9, name is 4-Chloro-5-fluoroindoline-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 84378-94-9, HPLC of Formula: C8H3ClFNO2

(b) 7.8 g (0.039 mol) of 4-chloro-5-fluoro-isatin are suspended in 50 ml of 100 percent acetic acid, treated with 0.25 ml of concentrated sulphuric acid and then 4.4 ml (0.043 mol) of 30 percent hydrogen peroxide are added dropwise thereto. The mixture is subsequently heated to 70 for 2.5 hours, then cooled to 10 and filtered. The crude product is recrystallized from acetone/hexane, there being obtained 6-chloro-5-fluoro-isatoic acid anhydride of melting point 275-278 (decomposition).

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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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5,7-Dimethylindoline-2,3-dione

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

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.

Synthetic Route of 5428-09-1,Some common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-1,3-dione, molecular formula is C11H9NO2, 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.

Following a slightly modified procedure,3 14 (222 mg, 1.0 mmol, 1.0 equiv) was dissolved in 1 mL of ethylacetate to obtain a 1 M solution. The solution was warmed up to 80 °C with 2-allylisoindoline-1,3-dione(374 mg, 2.0 mmol, 2.0 equiv). After 15 minutes of reflux under nitrogen, DLP (40 mg, 0.1 mmol, 0.1equiv) was added and the solution was stirred 1 hour and monitored by TLC. The crude was concentratedin vacuo and purified by flash column chromatography (PE:EtOAc 80:20 to 70:30) to afford pure 26 (370mg, 0.9 mmol, 90percent) as a light yellow oil and as a mixture of diastereoisomers. Rf (PE:EtOAc 8:2) = 0.12.1H NMR (CDCl3, 400 MHz) delta 7.84-7.80 (m, 2 H, ArH), 7.73?7.69 (m, 2 H, ArH), 4.60-4.49 (m, 2 H,OCH2CH3), 4.27-4.15 (m, 1 H, CHS), 4.03-3.88 (m, 2 H, CH2N), 3.35-3.20 (m, 2 H, CH2S), 2.78-2.64 (m,1.5 H, CH2CH2S, CHCOS), 2.60-2.54 (m, 1 H, CH2CH2S), 2.28-2.18 (m, 1 H, CHCH2CH), 2.05-1.95 (m,0.5 H, CH2CHS), 1.92-1.81 (m, 0.5 H, CH2CH2S), 1.75-1.65 (m, 1 H, CHCH2CH), 1.38 (t, 1.5 H, J = 7.1Hz, OCH2CH3), 1.37 (t, 1.5 H, J = 7.1 Hz, OCH2CH3). 13C NMR (CDCl3, 101 MHz) delta 212.5 (CS2), 212.3(CS2), 209.3 (COS), 209.2 (COS), 168.1 (N(CO)2), 134.2 (ArH), 131.7 (Ar), 123.5 (ArH), 70.6 (OCH2CH3),70.4 (OCH2CH3), 49.5 (CHCOS), 48.3 (CHS), 41.8 (CH2N), 40.3 (CH2N), 32.7 (CH2CH2S), 32.4(CH2CH2S), 32.1 (CHCH2CH), 31.8 (CHCH2CH), 30.3 (CH2CH2S), 30.2 (CH2CH2S), 13.7 (OCH2CH3).COSY, HSQC and HMBC were consistent with this attribution. IR 1773 (NC=O), 1718 (SC=O, NC=O),1223 (SC-O), 1048 (C=S). HRMS (EI) calculated for C18H19NO4S3 [M+] 409.0476; found 409.0481, fragmentationcalculated for C15H14NO3S [M+] 288.0694; found 288.0689.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Allylisoindoline-1,3-dione, its application will become more common.

Application of 446292-08-6, 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 446292-08-6 as follows.

2-{{(5S)-2-Oxo-3-(4-(3-oxo-4-morpholinyl)phenyl]-l,3-oxazolidin-5-ymethyr|- lH-isoindole- l ,3(2H)-dione ( 100 gm) and ethanol (1500 ml) charged into flask. Added methylamme (40%) solution (230 ml) at ambient temperature. Refluxed for one hour.After completion of reaction distilled off solvent completely. Charged pyridine ( 3,9 L) to the mass, cooled to 5C. Added 5′- chlorothiophene-2-carbonyichloride (51.5 gm) . Raise the. temperature to ambient temperature maintained for one hour and further extracted with, methylene chloride. The organic phase dried with sodium sulphate. Concentrated the organic layer under reduced pressure to obtain Rivaroxaban,

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Application of 954-81-4, A common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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.

[69] Potassium carbonate (13.57 g, 98.20 mmol), pyrrolidine (4.47 ml, 54.01 mmol) and sodium iodide (7.359 g, 49.098 mmol) were added to ethanol/acetone (1:1) at room temperature and stirred for 1 hour. To the reaction mixture was slowly added N – (5-bromopentyl)phthalimide (2) (10.60 g, 49.10 mmol), and the resulting reaction mixture was refluxed at 50 0C for 24 hours. After the reaction was completed, the resulting white solid was filtered and the solvent was evaporated under reduced pressure. Afterwards, the obtained residue was extracted with a saturated IN NaOH aqueous solution and dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane :methnol: ammonia water = 100:9:1) to give the target compound (3.27 g, 45 %).[70] 1H-NMR (400 MHz, CDCl3) delta 7.81-7.66 (m, 4H, aromatic), 3.66-3.63 (t, 2H, -CH2 -(CH2)4-NC4H8), 2.51-2.49 (t, 4H, -(CH2)S-NC2H4C2H4), 2.45-2.41 (m, 4H, -(CH2)5-NC2 H4C2H4), 1.77-1.74 (m, 2H, -(CH2VCH2-NC4H8), 1.68-1.55 (m, 4H, -CH2-CU2-CU2 – CH2-CH2-NC4H8), 1.36-1.32 (m, 2H, -CH2-CH2-CH2 -CH2-CH2-NC4H8).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

317-20-4, name is 7-Fluoroisatin, 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. Computed Properties of C8H4FNO2

Is added to the reactor 198 mg (1.2 mmol) 7 – fluoro – isatin and 144.1 mg (1.44 mmol) 2, 4 – pentanedionato, add 50 ml tetrahydrofuran and 5 ml DMF as the reaction solvent, adding 1 ml H2O2And 14.5 mg ZnCl2As the catalyst, the electric jacket is heated to 85 C, magnetic stirring reflux reaction for 12 hours. Thin-layer chromatographic trace to after the reaction is complete, evaporating the solvent under reduced pressure, the filter cake is tetrahydrofuran washing, drying to obtain the target compound 175.5 mg, total yield 59.2%.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference of 959235-95-1, A common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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.

HATU (7.02 g, 18.5 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (2.5 g, 12.31 mmol), 2-(4-chloro-2-fluorophenyl)acetic acid [CAS 194240-75-0] (2.32 g, 12.3 mmol) and diisopropylethylamine (6.1 ml_, 36.9 mmol) in DMF (100 ml_). The resulting mixture was stirred at room temperaure for 12 h. The mixture was diluted with water and the precipitate was filtered off and washed with water. The residue was taken up with EtOAc and the organic layer was washed with a 10% solution of K2CO3 in water, washed with brine, dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. The crude product was crystallized from diisopropyl ether to give 2- (4-chloro-2-fluorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 6a (4 g).

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, Product Details of 129487-92-9

Example V; tert-butyl 5-(3,5-dichloro-phenylsulphonylamino)-2,3-dihvdro-indole-1- carboxylate6 g tert-butyl 5-amino-2,3-dihydro-indole-1-carboxylate are dissolved in 50 ml of pyridine and 50 ml dichloromethane. To this is added dropwise a solution of 6.5 g 3,5-dichlorophenylsulphonyl chloride in 50 ml dichloromethane and the mixture is stirred for 1 hour at ambient temperature. Then it is diluted with dichloromethane and washed with 1 N hydrochloric acid and with saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 70:30 to 30:70). Yield: 8.6 g (76 % of theory)Mass spectrum (ESI+): m/z = 460 [M+NH4]+

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, tert-Butyl 5-aminoindoline-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, 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 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 × 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.