Tag: M.W=200-300

Electric Literature of 106976-23-2, These common heterocyclic compound, 106976-23-2, name is 5-Bromo-6-methylindoline-2,3-dione, 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 solution of 5-bromo-6-methyl-indoline-2,3-dione (980 mg, 4.08 mmol) in tetrahydrofuran (50 mL) at 0 C. was added NaBH4 (124 mg, 3.26 mmol). The mixture was stirred at 0 C. for 10 min. H2O (50 mL) was added and the mixture extracted with EtOAc (3*200 mL). The combined extracts were washed with brine (100 mL), dried with Na2SO4, filtered and concentrated to give crude 5-bromo-3-hydroxy-6-methyl-indolin-2-one (650 mg, 2.5 mmol, 61% yield) as a brown solid. LCMS (ESI) [M+Na]+=265.9.

Statistics shows that 5-Bromo-6-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 106976-23-2.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
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Application of 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.

To a mixture of 6-bromooxindole (Procedure D, 0.50 g, 2.4 mmol), vinyltributylstannane (0.95 g, 3.0 mmol), lithium chloride (0.03 g, 7.1 mmol), 2,6-di-tert-butyl-4-methylphenol (0.01 g, 0.05 mmol) in acetonitrile (25 ml) stirring at 80 C. was added dichlorobis(triphenylphosphine)palladium (II). The resulting reaction was stirred with heating for 16 h. The reaction was poured into a vigorously stirring mixture of 5M potassium fluoride solution: ethyl acetate/ 1:1 (250 mL) and stirred for 0.75 h. The resulting biphashic mixture was filtered through a Celite 521 pad and the pad flushed with ethyl acetate (5¡Á2 mL). The combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL) and filtered through Whatman PS 1 paper and evaporated in vacuo to a golden yellow syrup. The syrup was titurated with diethyl ether to yield several crops of tan solid. Pure samples were combined, slurried with diethyl ether, filtered, and air dried to yield 0.12 g (31%) of 6-vinyloxindole: 1H NMR (DMSO-d6): delta 10.36 (s, 1H), 7.13 (d, 1H, J=7.7 Hz), 6.98 (d, 1H, J=7.5 Hz), 6.66 (dd, 1H, J=10.9, 17.7 Hz), 5.70 (d, 1H, J=17.6 Hz), 5.18 (d, 1H, J=10.9 Hz), 3.42 (s, 2H).

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, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 169037-23-4

General procedure: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Huang; Xu, Yong; Mao, Fei; Zhu, Jin; Jiang, Hualiang; Li, Jian; Tetrahedron Letters; vol. 56; 4; (2015); p. 586 – 589;,
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Related Products of 18711-13-2, A common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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: A reaction flask with high vacuum valve was charged with 2-amino-N?-arylbenzohydrazides (1.0 mmol), 4-halogenated isatins (1.0 mmol), CuI (10 mg, 0.05 mmol), and Cs2CO3 (650 mg, 2.0 mmol). After being degassed by three freeze-thaw pump cycles, THF (10.0 mL) was injected into the mixture. And then, the reaction mixture was stirred at reflux for 10-16 h before reaching completion, which was monitored by TLC. The solvent was recovered by distillation under reduced pressure, and the residue was purified by chromatography over silica gel to give 3 using ethyl acetate and petroleum ether (1:2) as an eluent.

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.

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
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These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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. Application In Synthesis of 5-Bromoisoindolin-1-one

[0264] 5-Bromo-2,3-dihydro-isoindol-l-one (l.OOg, 4.72mmol), l-bromomethyl-4-methyl-benzene (1.14g, 6.14mmol) and cesium carbonate (3.08g, 9.44mmol) were suspended in anhydrous NMP (lOmL). The mixture was immersed in a 60C oil bath for 16.5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Column chromatography (20% to 40% ethyl acetate/hexanes) provided the title compound as a yellow solid (1.18g, 79%). 1H NMR CDC13: 7.76 (d, 1H), 7.62 (d, 1H), 7.55 (s, 1H), 4.76 (s, 2H), 4.24 (s, 2H), 2.35 (s, 3H).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
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Electric Literature of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 solution of tert-butyl 5-bromoisoindoline-2-carboxylate (32-1) (300 mg, 1.00 mmol) in dioxane and water (2.5 ml), was added 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridine (25-1) (459 mg, 1.10 mmol) and potassium phosphate (636 mg, 3.00 mmol) at room temperature. The reaction mixture was purged with argon for 5 minutes followed by addition of Pd(dppf)Cl2-DCM (40.8 mg, 50.0 mumol) at room temperature. The reaction mixture was heated to reflux overnight. After completion of reaction (monitored by TLC Rf = 0.4 in 20% ea/ hexane and LCMS), the reaction mixture was filtered and concentrated. The crude residue was purified by flash column (elution with 15 % EtOAc/Hexanes) to afford tert-butyl 5-(2,6- bis(benzyloxy)pyridin-3-yl)isoindoline-2-carboxylate (32-2) (330 mg, 648 mumol, 64.9 %) as a gummy liquid.1H NMR (400 MHz, DMSO-d6) delta 7.65-7.63 (m, 1H), 7.45-7.44 (m, 2H), 7.40-7.38 (m, 2H), 7.36-7.21 (m, 7H), 7.19 (m, 1H), 6.54 (m, 1H), 5.37 (br s, 4H), 4.63-4.60 (m, 2H), 4.43 (br s, 2H), 1.44-1.39 (m, 9H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
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These common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, 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. Application In Synthesis of 2-(3-Oxobutyl)isoindoline-1,3-dione

Prepare a cold (0C) solution OF 2- (3-OXOBUTYL) ISOINDOLE-1, 3-dione (6. 8 g, 31.5 mmol) in methanol (50 mL). Add Br2 (3.2 mL, 63 MMOL). Allow the reaction to warm to room temperature and stir for 15 hours. Add 10 M sulfuric acid (26 mL) and stir the mixture for 15 hours. Filter off the solids and dry in vacuo to afford 2- (4-BROMO-3- oxobutyl) ISOINDOLE-1, 3-dione (2.3 g). 1H NMR (CDCl3) 8 7.85-7. 90 (m, 2H), 7. 69-7.77 (m, 2H), 4.05 (t, J= 7 Hz, 2H), 3.96 (s, 2H), 3.15 (t, J= 7 Hz, 2H).

The synthetic route of 2-(3-Oxobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/9941; (2005); A1;,
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Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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 solution of LiHMDS (4.54 mL, M in THF) in THF (11 mL) was added at -78C a solution of intermediate E.ii (1.0 g, 3.78 mmol) in THF (3 mL) over 10 min. After stirring for 1 h at -78C a solution of N-(bromomethyl)phthalimide (1-09 g, 1.2 eq.) in THF (4 mL) was added dropwise over 10 min. The mixture was stirred at -78C for 1 h and then at rt overnight. The resulting solution was quenched with INHCl and extracted with DCM. The combined org. layers were washed with water, dried over MgSO4, concentrated and purified by CC (Hept/EA 1 :1) to afford the title intermediate as an off- white solid (0.361 g, 43% yield).MS (ESI, m/z): 424.4 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); A1;,
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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. Safety of 6-Bromoindolin-2-one

n-BuLi (2.5M in hexane, 158 mL, 396 mmol) was added dropwise to a stirred and cooled (-40C) suspension of 6-bromoindolin-2-one (21.0 g, 99 mmol) and i-Pr2NH (29.4 mL, 208 mmol) in dry THE (225mL) under Ar. During addition the temperature is maintained below -20C. After complete addition, the temperature was allowed to warm to 0C, then a solution of 1 ,2-dibromoethane (25.6 mL, 297 mmol) in dry THF (25 mL) was added dropwise maintaining a temperature of below 10C. After complete addition, the reaction mixture was stirred at room temperature for 1 8h. The reaction mixture was concentrated to a smaller volume (-75 mL) under reduced pressure.The residue was diluted with EtOAc (200 mL) and brine (100 mL). The biphasic mixture was then stirred vigorously. The pH of the solution was brought to a value of 5 by slowly adding 4M aqueous HCI (-50 mL). The biphasic system was filtered through a glass filter in order to remove the solids which appeard in the bisphasic system. The solids were rinsed with EtOAc (-10 mL), collected and dried on the air to give a first batch of INT-1 as a pale solid (13.99 g, 58.8 mmol, 59.3%).The filtrate layers were separated. The aqueous phase was extracted with EtOAc (2x 100 mL). The combined organic phases were washed with brine (100 mL), dried over Na2SO4 and the solvent was distilled off. The viscous dark-brown residue was stirred with EtOAc (25 mL) for 5 mm at rt. The suspension was then slowly diluted with heptane (75 mL) while stirring which again resulted in solids which were filtered off, rinsed with heptane (10 mL), collected and air-dried to give a second batch of INT-1 (1)as a brown solid (6.04 g, 25.4 mmol, 25.6%).LCMS: calculated for [M+H]: 238/240, found: 238/240, mono-Br isotope pattern observed.

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

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
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Application of 41663-84-7, A common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione, molecular formula is C9H6N2O4, 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 4 To a reaction vessel containing dimethylacetamide (25 ml) were added 4-nitro-N-methylphthalimide (0.50 g, 0.00243 mol), biphenyl (0.204 g, 0.00132 mol) and sodium hydrogen sulfide (0.14 g, 0.0025 mol). The reaction was allowed to proceed at 70 C. 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% (0.035 g).

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

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
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