Category: 99365-40-9

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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 99365-40-9

a) 6-Bromo-1,3,3-trimethylindolin-2-oneUnder an argon atmosphere NaH (60 % on mineral oil, 7.32 g, 183 mmol) was suspended in dry THF (45 ml). A suspension of 6-bromoindolin-2-one (10 g, 45.7 mmol) in dry THF (108 ml) was added in portions during 10 minutes while temperature was kept below 27 C. The reaction mixture was warmed to 25 C and Mel (11.4 ml, 183 mmol) was added dropwise during 1 hour while the internal temperature was carefully kept between 24 and 27 C. The reaction mixturewas stirred at room temperature for 18 hours. Saturated aqueous NT-L1C1 solution (20 ml) was carefully added at 10-15 C. The mixture was diluted with EtOAc, H20 and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc, the organic layers were washed with saturated aqueous NaHCO3 solution, combined and dried with Na2504. The solvent was evaporated and the residue was purified by silica gel chromatography using heptane / ethylacetate as eluent. The title compound was obtained as light red solid (7.0 g). Mixed fractions were purified again by preparative HPLC yielding further 3.1 g of the title compound.MS ESI (m/z): 254.1, 256.2 [(M+H)i.1H NMR (CDC13, 300 MHz): oe = 7.19 (dd, J=1.5, 7.8 Hz, 1H), 7.06 (d, J=7.9 Hz, 1H), 6.99 (d, J=1.6 Hz, 1H), 3.19 (s, 3H), 1.35 (s, 6H).

The synthetic route of 99365-40-9 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; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
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99365-40-9, Adding some certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-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 99365-40-9.

Potassium tert-butoxide (6.2 g) was suspended in tetrahydrofuran (55 mL), and a suspension of 6-bromo-1,3-dihydroindole-2-one (2.3 g) in tetrahydrofuran (39 mL) and copper (I) bromide dimethyl sulfide complex (252 mg) were added. To the reaction mixture, methyl iodide (1.9 mL) was added at 0C, and then the reaction mixture was stirred at 0C for 5 minutes, and subsequently stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous solution of ammonium chloride was added, and the reaction mixture was 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 (1.4 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.65 (1H, brs), 7.18 (1H, dd, J = 7.8, 2.0 Hz), 7.06 (1H, d, J = 2.0 Hz), 7.05 (1H, d, J = 7.8 Hz), 1.38 (6H, s). ESI-MS found: 240 [M+H]+

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 99365-40-9.

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,
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99365-40-9, 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. 99365-40-9 name is 6-Bromoindolin-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.

Preparation 1: 6-Iodooxindole A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar(g) and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar(g) (3 times). Racemic trans-N,N’-dimethyl-1,2-cyclohexanediamine (74 muL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110 C. for 24 h. The reaction was then cooled to room temperature and 15% NH4OH(aq) (50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
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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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 99365-40-9

Pottasium tert-butoxide (0.085 g, 0.80 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at ambient temperature, the mixture was heated to 40-45 C and methyl acrylate (4.00 mL, 44.40 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.00 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85 C for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid. LRMS (m/z): 292/294 (M-1)-. 1H-NMR delta (DMSO-d6): 1.99-2.08 (m, 2H), 2.13-2.22 (m, 2H), 2.41-2.50 (m, 2H), 2.82-2.92 (m, 2H), 7.07 (d, J=3.0 Hz, 1H), 7.21 (dd, J=9.0/3.0 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 10.70 (br s, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, Name is 6-Bromoindolin-2-one, 99365-40-9, 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.

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and thiophene-3-boronic acid (4.3 g, 33.6 mmol). The mixture was stirred at 100 C. in an oil bath for 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (500 mL), washed with IN hydrochloric acid (200 mL), water (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give a black solid. The solid was triturated with methylene chloride to give 2.02 g (36%) of 6-thiophen-3-yl-1,3-dihydroindol-2-one as a purple-gray solid. 1H NMR (360 MHz, DMSO-d6) delta 10.49 (s, 1H, NH), 7.77 (s, 1H, Ar-H), 7.59 (m, 1H, Ar-H), 7.45 (m, 1H, Ar-H), 7.24 (m, 2H, Ar-H), 7.07 (m, 1H, Ar-H), 3.46 (s, 2H, CH2CO). MS m/z: 215 [M]+.

Statistics shows that 6-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 99365-40-9.

Reference:
Patent; Sugen, Inc.; US6689806; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 99365-40-9 name is 6-Bromoindolin-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. 99365-40-9

(293-1) 3,3-Dimethyl-6-bromoindolin-2-one A solution (50 ml) of 6-bromoindolin-2-one (3.18 g) in THF was cooled to -78 C. and 1.5 M lithium diisopropylamide (20 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction mixture was brought to room temperature and stirred for 1 hr. Then the reaction solution was cooled to -78 C. again and 1.5 M lithium diisopropylamide (10 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction solution was brought to room temperature with stirring. Then a saturated aqueous solution of ammonium chloride was added thereto and the resultant mixture was extracted with ethyl acetate. The residue was washed with hexane to give the title compound (3.35 g) as a white amorphous solid (yield: 93.0%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.38(6H, s), 7.05(1H, d, J=8.0Hz), 7.096(1H, d, J=1.6Hz), 7.169(1H, d, J=1.6Hz), 8.41(1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 99365-40-9

To a stirred mixture of 6-bromoindolin-2-one A.35 (5.0 g, 23.6 mmol) and NaHCO3 (10 eq., 21.0 g) in THF (130 mL) was added (Boc)2O (2.5 eq., 14.0 g) at room temperature under N2. The resulting mixture was heated at reflux for 3 h. After cooling, the mixture was vacuum filtered through a layer of celite and the filter cake was thoroughly washed with THF. The filtrate was concentrated in vacuo and the residue was subjected to combi-flash column chromatography (ethyl acetate/hexanes) to give tert-butyl 6-bromo-2-oxo-2,3-dihydro-lH- indole-1-carboxylate A.36 (6.0 g, 81% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.04 (1 H, d, J=I.6 Hz), 7.29 (1 H, dd, J=8.0, 1.8 Hz), 7.1 1 (1 H, d, J=7.8 Hz), 3.60 (2 H, s), 1.65 (9 H, s). LCMS-ESI (POS), M/Z, M+Na+: Found 334.0 and 336.0.

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem