Category: 71294-03-6

Reference 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.

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.

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

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. 71294-03-6, name is 7-Fluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 7-Fluoroindolin-2-one

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]+).

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:
Patent; Wyeth; US2007/72928; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

71294-03-6, A common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

7-Fluorooxindole (1.28 g, 8.50 mmol) and lithium chloride (0.899 g, 21.3 mmol) were suspended in 80 mL of THF and cooled to 0 C. n-Butyllithium (8.5 mL, 16.9 mmol) was added slowly, the mixture was stirred for 20 minutes, and then dibromoethane (0.73 mL, 8.5 mmol) was added. The mixture was warmed to 25 C. and stirred for 16 hours. The reaction was quenched with saturated aqueous NH4Cl and diluted with ether. The organics were washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (10% acetone/hexane) afforded 0.54 g (36%) of 7′-fluorospiro[cyclopropane-1,3′-indol]-2′(1’H)-one as a white solid

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

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

71294-03-6, A common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

To a stirred slurry of potassium tert-butoxide (185 g, 1.65 mol) in tthetatrahydrofuran (1350 mL) was added 7-fluoro-oxindole (50 g, 0.33 mol) and copper (I) bromide-dimethyl sulfide complex (7 g, 0.033 mol). Methyl iodide (150 g, 1.06 mol.) was added to the mixture at 5-100C. The reaction mixture was stirred at 20- 25C for 1 hour. 10% NH4CI (1000 mL) was added to the reaction mixture. The two layers were separated. The organic layer was concentrated via vacuum distillation at 25-400C to reach a volume of 250 mL. The aqueous layer is extracted with tert- butyl methyl ether (2 x 500 mL). The concentrated organic layer and tert-butyl methyl ether extraction layers were combined and washed with 15% NaCI (250 mL). The organic solution was filtered through silica gel (100 g). Heptane (1250 mL) was added to the filtrate. The mixture was concentrated under atmosphere at 60-950C to reach a volume of 700 mL. The concentrate was cooled to 0-50C from 85-95C over 2 hours to crystallize. Solid was filtered, washed with heptane (100 mL), and oven- dried to give 41 g (69.4%) of a beige solid 7-fluoro-3, 3-dimethyl-oxindole, 92% w/w purity by HPLC.

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

Reference:
Patent; WYETH; WO2008/24492; (2008); A2;,
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. 71294-03-6

Example 9 Preparation of 3-(4,6-diethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one 7-Fluoro-1,3-dihydro-2H-indol-2-one (1.0 g) is introduced as initial charge in 10 ml of N,N-dimethylacetamide. A solution of potassium carbonate (1.8 g) and potassium hydroxide (0.3 g) in 10 ml of water is added and the mixture is briefly after-stirred. Then, a solution of 2-chloro-4,6-diethoxy-1,3,5-triazine (3.0 g, ca. 50% purity) in 10 ml of N,N-dimethylacetamide, and 10 ml of water are added. A solid separates out from the clear yellow solution. The mixture is stirred at room temperature and further 2-chloro-4,6-diethoxy-1,3,5-triazine (1 g, ca. 50% purity) is added in two portions after 2 and 18 hours. The mixture is stirred for a further 3 hours at 30 C., admixed with 10 ml of toluene, adjusted to pH 1-2 with hydrochloric acid (10%) and after-stirred for 30 min. The solid is filtered off with suction, washed twice alternately with water and heptane and dried. This gives the title compound as solid in an HPLC purity of 99% area (1.53 g, 72% of theory). LC-MS: M+H=319 (86%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.3 (s, 1H), 7.59 (d, 1H), 6.96 (dd, 1H), 6.93-7.00 (m, 1H), 4.50 (q, 4H), 1.37 (t, 6H).

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

71294-03-6, A common compound: 71294-03-6, name is 7-Fluoroindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

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) portionwise within 20 minutes. The reaction mixture was stirred for 30 minutes. Mel (31.2 g, 13.7 ml, 220 mmol) was added dropwise at 24-27 Cwithin 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 10-15 C, 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 gelchromatography using ethyl acetate heptane as eluent. The title compound was obtained as orange crystals (9.91 g).MS ESI (mz): 194.3 [(M+H)j.1H NMR (CDC13, 400 MHz): 8(ppm) = 6.99-6.97 (m, 3H), 3.43 (d, J = 2.62 Hz, 3H), 1.37 (s, 6H).

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, 7-Fluoroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 71294-03-6, name is 7-Fluoroindolin-2-one, 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 71294-03-6. 71294-03-6

7-Fluorooxindole (1.51 g, 10 mmol) and lithium chloride (1.06 g, 25 mmol) were suspended in 30 mL of THF and cooled to 0 C. n-Butyllithium (10 mL, 20 mmol) was added slowly and the mixture was stirred for 20 minutes. Iodomethane (1.24 mL, 20 mmol) was added and the mixture was stirred at 0 C. for 1 hour then warmed to 25 C. and stirred for 16 hours. The reaction was quenched with saturated aqueous NH4Cl and diluted with ethyl acetate. The organics were washed with water, saturated aqueous NaCl, dried over MgSO4, and concentrated. Flash chromatography (5% acetone/hexane) afforded the title compound 0.12 g (7%) as a white solid.

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 7-Fluoroindolin-2-one.

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