Indolines-derivatives

Electric Literature of 19155-24-9,Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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.

PREPARATION 1; 5-(2-Chloroacetvl)-3w3-dimethvl-1 3-dihvdroindol-2-one; A 12.5 L 4-neck flask equipped with a mechanical stirrer, reflux condenser and two stoppers and heating mantle, was charged with AICI3 (633.29 g, 4.75 mol), 2 L of carbon disulfide and chloroacetyl chloride (87 mL, 1.09 mol) and this was stirred at room temperature (rt) during the portionwise addition of 3, 3-dimethyl-1, 3-dihydro- indol-2-one (123.5 g, 0.766 mol). This mixture was then heated to reflux for 3 hours, then cooled overnight. The solvent was decanted and the reaction was quenched with addition of ice and water (8 L). The suspension was stirred vigorously for 1.5 hours, followed by filtration. The solids were washed with water (4.2 L) and then dried overnight in a vacuum oven at 50 degrees Celsius (°C) (192.19 g of 5- (2- chloroacetyl)-3, 3-dimethyl-1, 3-dihydroindol-2-one). 29.54 g of this material was taken up in hot acetone and purified by flash chromatography (250 g silica gel) eluting with acetone which provided >96percent pure 5-(2-chloroacetyl)-3, 3-dimethyl-1, 3- dihydroindol-2-one by HPLC. Yield = 15.54 g (52percent); MS (APCI), (M + 1) + = 238. Anal. calculated for C12H12CINO2 : C, 60.64 ; H, 5.09 ; N, 5.89. Found: C, 61.04 ; H, 5.15 ; N, 5.38percent.

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

These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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. Safety of 5-Bromoindoline

Part 1. To a solution of 5-bromoindoline (1.0 g, 5 mmol) in 10 ml of dioxane was added 5 mL of a 1N NaOH solution and 5 mL of water. This mixture was cooled with an ice bath, and di-tert-butyl dicarbonate (1.2 g, 5.5 mmol) was added in one portion. The reaction was allowed to warm to room temperature, stirred for 4 hours, and then concentrated. The residue was extracted with ethyl acetate (2*25 mL), and the combined organic phases were washed with water (2*25 mL), saturated aqueous NaCl (2*25 ml), then dried over MgSO4. Filtration and concentration in vacuo gave N-Boc-5-bromoindoline (1.33 g, 89%) as a light brown powder after drying. 1H NMR (CDCl3) delta: 1.541 (s, 9H); 3.03-3.08 (t, 2H); 3.92-3.96 (t, 2H); 7.23-7.27 (m, 3H).

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

Reference of 118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

The synthetic route of 6-Chloro-5-(2-chloroethyl)indolin-2-one has been constantly updated, and we look forward to future research findings.

Electric Literature of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A 4-N-methylphthalimide/water wet cake (50.0 grams (g) dry weight, containing 10-60% water), resulting from either a mixed acid (H2SC /HNO3) nitration of N- methylphthalimide or an all nitric acid nitration of N-methylphthalimide, was charged to a 1000 mL, single-necked (24/40 joint) round-bottomed flask, equipped with a magnetic stir bar, and means to heat the flask with an external temperature controlled oil bath. The flask was then charged with 367 g of toluene, and enough additional deionized water was added such that the total amount of water present in the flask was equal to 160 g. The amount of water used targeted 20 to 25 wt% of 4NPI with respect to the total weight of 4NPI and water. The reaction mixture was magnetically stirred with an oil bath set temperature of 90C. After the 4NPI had dissolved in the toluene the stirring was stopped, and the lower water phase was removed via pipette. This method of dissolution and separation of the 4NPI toluene phase from the aqueous phase constitutes a purification of the 4NPI as water soluble impurities were extracted from the 4NPI/toluene phase into the aqueous phase. This dissolution/separation method is termed herein the “4NPI Extraction.” The 4NPI toluene solution was then placed on a roto-evaporator, equipped with a hot oil bath to heat the flask, and plumbed to a cold trap connected to a vacuum pump. The flask was rotated in the hot oil bath (temperature controlled at 110C) and the solvent was removed under reduced pressure (<30 mm). Once the majority of toluene had been removed, the flask was allowed to rotate in the oil bath at 110C, 25 mm, for 60 minutes, to afford a dry solid free of toluene and water. The solid was transferred to a glove box inerted with dry nitrogen. The desired dried catalyst (HEGC1, TBAB, or C6B) was added to the dried 4NPI for the bisimide forming reaction. The synthetic route of 2-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxyindolin-2-one

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromoindoline

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12) To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in MeCN (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with Et2O and washed with water and brine solution (2*). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as a off-white solid, which was used in the next step without further purification (3.0 g).

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.

Application of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-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: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

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.

Example 2. To a reaction vessel containing dimethylacetamide (25 ml) were added 4-nitro-N-methylphthalimide (0.50g, 0.00243 mol), biphenyl (0.204g, 0.00132 mol) and sodium hydrogen sulfide (0.14g, 0.0025 mol). The reaction was allowed to proceed at 70C for 24 hours. samples of the reaction mixture were taken and examined by HPLC methods. A yield of 16.3% 4,4’bis(N-methylphthalimide)sulfide was indicated. The isolated yield was 15% (0.035g).

The synthetic route of 41663-84-7 has been constantly updated, and we look forward to future research findings.

Electric Literature of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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.

Example 2: Preparation of 7V-(2-(hvdroxycarbamoyl)ethyl)5-(YZ)-(5-fluoro-2- oxoindolin- 3-ylidene)methvD-2,4-dimethyl-lH-pyrrole-3- carboxamide (compound 2) Step 2a. Methyl 3-(5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl) -2,4- dimethyl- lH-pyrrole-3-carboxamido)propanoate (compound 110-2 ) To a stirred solution of 1 (0.5 g, 1.67 mmol) in DMF( 35 mL) at room temperature was added HOBt(1.02 g, 7.52 mmol), triethylamine (2.12 mL, 15.03 mmol), ECDI-HCl(1.44 g, 1.52 mmol) and methyl 3-aminopropanate hydrochloride^.7 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the pH of solution was adjusted to 11-12 with 10 mol/L NaOH. The mixture was filtrated and the solid was collected washed with water, dried to obtain crude yellow solid product 110-2 (0.44 g, 68.3%). LCMS: m/z 386(M+1), 1H NMR(DMSO-^6) delta2.38 (s, 3H), 2.41 (s, 3H), 2.50 (t, 2H),3.44 ( t, 2H), 3.62 (s,3H), 6.85 (m, 2H), 7.71 (m,3H), 10.86 (s, IH), 13.69 (s, IH).

The synthetic route of 356068-93-4 has been constantly updated, and we look forward to future research findings.

Application of 20870-90-0, 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 20870-90-0 as follows.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

According to the analysis of related databases, 20870-90-0, the application of this compound in the production field has become more and more popular.