Category: 71294-03-6

Electric Literature of 71294-03-6,When developing chemical systems it’s of course important to gain a deep understanding of the chemical reaction process.

7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) was dissolved in THF (200 mL). The solution was then cooled to -78 C. and n-butyllithium (2.5 M, 40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate, dried (MgSO4), and concentrated in vacuo. Flash chromatography (SiO2, Hexane/ethylacetate 9/1 then 8/2) gave 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g, 48%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2006/9509; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

40 g of 7-fluoroanthraquinone was added to 450 ml of anhydrous methylene chloride, 15 g of aluminum trichloride was added, 60 g of oxalyl chloride was added, the mixture was heated to reflux for 2 hours, cooled to room temperature, and then water was added thereto for liquid separation, drying, and concentration. The residue was columned to give 47 g of 2-(7-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Cheng Jia; (6 pag.)CN107698483; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 71294-03-6, These common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-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.

Example 53Preparation of 5-f(2-(riS.2SV2-ri-(5-chloropyrimidin-2-vnpiperidin-4- yllcYclopropyUethy?aminol-T-fluoro- 1 ,3-dihvdro-2H-indol-2-oneStep 1: 7-fluoro-5-tauiitro-L3-dihvdro-2H-indol-2-one7-fluoro-1,3-dihydro-2H-indol-2-one (8.Og, 52.9 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x), and dissolved into EtOAc (1 L). TWs solution was washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 71294-03-6 as follows. Safety of 7-Fluoroindolin-2-one

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

According to the analysis of related databases, 71294-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 71294-03-6, name is 7-Fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 7-Fluoroindolin-2-one

a) 7-Fluoro- 1 ,3,3-trimethylindolin-2-one To a suspension of NaH (8.79 g, 220 mmol) in tetrahydrofuran (100 ml) was added 7- fluoroindolin-2-one (8.30 g, 54.9 mmol) in portion within 20 minutes. The reaction mixture was stirred for 30 minutes. Mel (31.2 g, 13.7 ml, 220 mmol) was added dropwise at 24-27C within 1.5 hours. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was very carefully quenched with 20 ml saturated aqueous ammonium chloride solution at 10-15C, then diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as orange crystals (9.91 g). MS ESI (m/z): 194.3 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 6.99-6.97 (m, 3H), 3.43 (d, J = 2.62 Hz, 3H), 1.37 (s, 6H).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 71294-03-6, 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. 71294-03-6 name is 7-Fluoroindolin-2-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.

7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) was dissolved in THF (200 mL). The solution was then cooled to -78 C. and n-butyllithium (2.5 M, 40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate, dried (MgSO4), and concentrated in vacuo. Flash chromatography (SiO2, Hexane/ethylacetate 9/1 then 8/2) gave 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g, 48%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2006/9509; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

Step 5: 7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) were dissolved in tetrahydrofuran (200 mL). The solution was cooled to -78 C. and n-butyllithium (40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified via Biotage chromatography (Flash40i, silica, 10% then 20% ethyl acetate/hexane) gave 4.1 g (48%) 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. MS (ESI) m/z 180, ([M+H]+).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2008/153873; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

Step 1a: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one (7) This is similar to the procedure described in G. W. Rewcastle, B. D. Palmer, E. M. Dobrusin, D. W. Fry, A. J. Kracker and W. A. Deny, Journal of Medicinal Chemistry, 1994, 37, 2033-2042. A suspension of the 7-fluoro-1,3-dihydro-indol-2-one (9, 1.0 g, 6.62 mmol.) in H2O (30 mL) and NaOH (0.397 g, 9.92 mmol., 1.50 eq.) was treated with dimethyl sulfate (1.24 g, 9.86 mmol., 1.49 eq., 0.933 mL; added all at once) and heated to 100 C. for approx. 10 min. and then allowed to cooled to about 50 C. An additional 1.0 eq. of NaOH (0.265 g) and then additional 1 eq. of dimethyl sulfate (0.835 g, 0.626 mL) were added. Again heated to 100 for approx. 10 min. Then cooled to 0 C. in an ice bath and stirred and then filtered off solids, washed several times with water and dried on buchner funnel under vacuum overnight to yield the title compound as a solid. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 3.4 (d, J=2.5 Hz, 3H) 3.5 (s, 2H) 6.9 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 71294-03-6, name is 7-Fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 71294-03-6

Example 1 Preparation of 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one Variant A: 7-Fluoro-1,3-dihydro-2H-indol-2-one (100 g) is introduced as initial charge in 600 ml of N,N-dimethylacetamide and cooled to ca. 0 C. with ice/methanol cooling. A solution of potassium hydroxide (43.2 g) and potassium carbonate (143 g) in 600 ml of water is added and the mixture is briefly after-stirred. Then, 2-chloro-4,6-dimethoxy-1,3,5-triazine (140.8 g) is added and in each case 100 ml of water and N,N-dimethylacetamide are used for after-rinsing. The cooling bath is removed, the mixture heats up to ca. 30 C. It is stirred for 18 hours at room temperature. After adding 150 ml of toluene, dilute hydrochloric acid (ca. 700 ml) is used to adjust the pH to 3-4 and at the same time some antifoam (Fluowet PL 80) is added. The solid is filtered off with suction, washed three times with in each case 250 ml of water and twice with in each case 250 ml of heptane and dried in vacuo at 55 C. This gives the title compound as solid in a purity of 96.6% (187.5 g, 95% of theory). LC-MS: M+H=291 (100%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.37 (s, 1H), 7.64 (d, 1H), 6.97 (dt, 1H), 6.86 (dd, 1H), 4.05 (s, 6H).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Karig, Gunter; Ford, Mark James; Siegel, Konrad; US2013/345422; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 71294-03-6, These common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-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.

Step 4 7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) were dissolved in tetrahydrofuran (200 mL). The solution was cooled to -78 C. and n-butyllithium (40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the crude product via Biotage chromatography (Flash40i, silica, 10% then 20% ethyl acetate/hexane) gave 4.1 g (48%) of 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. MS (ESI) m/z 180 ([M+H]+). Step 4:; 7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) were dissolved in tetrahydrofuran (200 mL). The solution was cooled to -78 C. and n-butyl lithium (40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified via Biotage chromatography (Flash40i, silica, 10% then 20% ethyl acetate/hexane) to give 4.1 g (48%) 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. MS (ESI) m/z 180, [M+H]+).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.