Category: 90725-50-1

Electric Literature of 90725-50-1, 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. 90725-50-1, name is 6-Bromo-3-methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The compound [78-1] obtained in the process (1) (4.9 g) was suspended in toluene (22 mL), and borane dimethyl sulfide complex (4.4 mL) was added at 0C, and then the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled with ice-water bath, and an aqueous solution of 5N-sodium hydroxide (8 mL), an aqueous solution of 8N-sodium hydroxide (8 mL) and ethyl acetate (8 mL) were added, successively, and then the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL), and triethylamine (4.55 mL) and a solution of di-tert-butyl dicarbonate (6.2 g) in tetrahydrofuran (10 mL) were added successively at room temperature, and then a grain of dimethylaminopyridine was added, and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (4.6 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 8. 03 (1H, s), 7. 07 (1H, dd, J = 7.9, 1.6 Hz), 6.96 (1H, d, J = 8.3Hz), 4.19-4.08 (1H, m), 3.57-3.43 (1H, m), 3.39-3.27 (1H, m), 1.53 (9H, brs), 1.30 (3H, d, J = 6.8 Hz). ESI-MS found: 256 [M-tBu+H]+

The synthetic route of 6-Bromo-3-methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); 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 90725-50-1 as follows. Computed Properties of C9H8BrNO

6-bromo-3 -methyl- 1, 3 -dihydro-2H-indol-2-one A.20 (500mg, 2.21mmol) and Cs2CO3 (1.44g, 4.42mmol) were combined in 4ml of DMF. To this was then added methyl bromoacetate A.21(203muL, 2.21mmol) and the solution was stirred at room temperature for 2 hours. After diluting the solution with water and adjusting the pH to 2 with IN HCl, the aqueous layer was and extracted with ethyl acetate. The organics were then concentrated under vacuum. The residue obtained was purified by CombiFlash chromatography eluting with a gradient of dichloromethane to 3%methanol/dichloromethane. The fractions containing the product were combined and concentrated under vacuum to give methyl (6-bromo-3-methyl-2-oxo-2,3- dihydro-lH-indol-3-yl)acetate A.22 (468mg) as an off white solid. ESI-MS: M – 296.0 m/z.

According to the analysis of related databases, 90725-50-1, the application of this compound in the production field has become more and more popular.

Synthetic Route of 90725-50-1, A common heterocyclic compound, 90725-50-1, name is 6-Bromo-3-methylindolin-2-one, molecular formula is C9H8BrNO, 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.

6-bromo-3 -methyl- 1, 3 -dihydro-2H-indol-2-one A.20 (15g, 66.35mmol) was combined with 70ml of acetic anhydride. The solution was heated at 1100C for 2 days before it was concentrated under vacuum. The oil obtained was diluted with ethyl acetate and washed in succession with saturated NaHCO3, water, and brine. The organics were dried over MgSO4 before they were concentrated under vacuum. The residue obtained was heated in EtOH (80ml) to form a clear reddish solution. After cooling to -150C and standing overnight, a light brown solid was collected by filtration as 1 -acetyl-6-bromo-3 -methyl- 1,3 -dihydro-2H-indol-2- one A.26 (8.8g, 50%) .IH NMR (500 MHz, DMSO-d6) delta ppm 8.25 (1 H, d, J=I.5 Hz), 7.43 (1 H, dd, J=7.8, 1.4 Hz), 7.38 (1 H, d, J=8.3 Hz), 3.78 (7 H, q, J=7.3 Hz), 2.56 (3 H, s), 1.42 (3 H, d, J=7.8 Hz).

The synthetic route of 90725-50-1 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 90725-50-1, These common heterocyclic compound, 90725-50-1, name is 6-Bromo-3-methylindolin-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.

[(2R)-2-(4-Iodophenyl)propyl][(methylethyl)sulfonyl]amine (0.295 g, 0.804 mmol) bis(pinacolate) diboron (0.224 g,0.882 mmol) PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol) and KOAc (0.0.276 g, 2.81 mmol) were combined and heated at 80 C. under nitrogen for 24 h. The mixture was allowed to cool to ambient temperature and 6-bromo-3-methyl-1,3-dihydro-1-indol-2-one (0.0.200 g, 0.885 mmol), PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol)), 2M Na2CO3 (2.0 mL, 5.0 mmol) respectively were added. The resulting mixture was heated and stirred at 80 C. overnight and worked up in a manner analogous to the procedure described in example 3 to provide the final title compound, 6-[4-((1R)-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]-3-methylindolin-2-one, (0.050 g). MS: 387(M+1).

Statistics shows that 6-Bromo-3-methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 90725-50-1.

Reference:
Patent; Bender, David Michael; Forman, Scott Louis; Jones, Winton Dennis; Smith, Daryl Lynn; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225127; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem