Indolines-derivatives

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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C14H11NO

General procedure: A mixture of oxindoles (2.0102 mmol), cinnamaldehyde,a base and a prescribed amount of TIPS-b-CDwas stirred in solvents(2 mL) at 10 C. After the removal of solvent in vacuo, the residuewas analyzed by 1H NMR to determine the reaction conversion andproduct distributions. The product was isolated by silica gel columnchromatography with a hexane/ethyl acetate (4:1, v/v) eluent. 4.5.12 (E)-N-Phenyl-3-(3′-phenylallylidene)-indolin-2-one ((E)-3g) Yellow prisms: mp 158-159 C, 1H NMR (DMSO-d6) delta 6.79 (d, J=7.7 Hz, 1H), 7.16 (dd, J=7.7, 7.7 Hz, 1H), 7.28 (dd, J=7.7, 7.7 Hz, 1H), 7.40-7.50 (m, 7H), 7.51 (s, 1H), 7.56-7.61 (m, 2H), 7.82-7.89 (m, 3H), 8.17 (d, J=7.7 Hz, 1H). 13C NMR (DMSO-d6) delta 109.0, 121.5, 122.7, 123.2, 124.2, 124.4, 126.9, 127.9, 128.3, 129.0, 129.2, 129.6, 130.0, 134.4, 135.8, 136.2, 142.8, 145.8, 166.9. IR: 1699.82 (C=O). HRMS (EI) m/z calcd for C23H17NO: 323.1310, found 323.1313.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Asahara, Haruyasu; Kida, Toshiyuki; Hinoue, Tomoaki; Akashi, Mitsuru; Tetrahedron; vol. 69; 45; (2013); p. 9428 – 9433;,
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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 17702-83-9 as follows. Application In Synthesis of 2-(8-Bromooctyl)isoindoline-1,3-dione

step 1 8-(Benzoxazol-2-ylsulfanyl)-octylamine To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) andDMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by N-(8-bromooctyl)phthalimide (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20percent EtOAc/petroleum ether gradient) to afford the thioether intermediate. To this thioether intermediate (3.02 g, 7.39 mmol) in MeOH (40 mL) at room temperature was added hydrazine monohydrate (0.860 mL, 17.7 mmol) and the resulting mixture was heated to reflux. After 18 h at this temperature, the reaction was concentrated, taken up in EtOAc (300 mL), and filtered to remove insoluble materials. This phthalimide byproduct was washed with excess EtAOc, and the filtrate was washed with H2O (40 mL) and brine (40 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (1.87 g, 57percent) as an oil; 1H NMR (CDCl3) delta1.14-1.67 (m, 12H), 1.72-1.92 (m, 2H), 2.69 (t, J=9.6 Hz, 2H), 3.32 (t, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 7.38-7.47 (m, 1H), 7.54-7.66 (m, 1H); mass spectrum [(+) ESI], m/z 279(M+H)+.

According to the analysis of related databases, 17702-83-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Butera, John A.; Caufield, Craig E.; Graceffa, Russell F.; Greenfield, Alexander; Gundersen, Eric G.; Havran, Lisa Marie; Katz, Alan H.; Lennox, Joseph R.; Mayer, Scott C.; McDevitt, Robert E.; US6214877; (2001); B1;,
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Synthetic Route of 423116-18-1, A common heterocyclic compound, 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, molecular formula is C15H15NO3, 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.

Sodium cyanoborohydride (48.5 g, 772 mmol) was added portionwise to a solution of 2-((4-oxocyclohexyl)methyl)isoindoline-1,3-dione (100 g, 389 mmol, Intermediate 34) in AcOH (1.0 L), and the resulting mixture was stirred at rt for 16 h. After this time, the mixture was concentrated, and the concentrate was dissolved in EtOAc. The resulting solution washed twice with a saturated aqueous NaHCO3 solution, dried with anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a colorless solid, which was used in the next step without further purification.

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:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (2019); A1;,
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Application of 3783-77-5, A common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, molecular formula is C12H11NO3, 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.

A mixture of 50 g of 2- (3-oxobutyl) isoindoline-1,3-dione, 14.3 g of ethylene glycol and 7.4 g of p-toluenesulfonium tetrahydrate were dissolved in 500 ml of anhydrous toluene and treated with a water separator Reflux for 24 hours. After completion of the reaction, the reaction system was saturatedNaHCO3 aqueous solution 500 ml twice. The aqueous phase was extracted twice with 500 ml of ethyl acetate. The organic phase is combined with anhydrous sulfur Dried over sodium carbonate, and the solvent was distilled off under reduced pressure to obtain a distillation residue which was recrystallized from ethanol to give 45 g of a yellow solid: 2- (2-(2-methyl-1,3-dioxolan-2-yl) ethyl) isoindoline-1,3-dione, yield: 74.8%.

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Yao Ming Kant, Immanuel New Drug Development Co., Ltd.; Yu Lingbo; Wang Ruile; Zhou Qiang; Xu Xueqin; Zhang Dawei; Bai Youyin; Chen Dongzhi; Gao Mingfei; Yao Baoyuan; Han Huaxin; Fu Xinyu; Ma Rujian; (5 pag.)CN106939001; (2017); A;,
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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. 193354-13-1, name is 5-Iodoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 ML of methanol, 15 ML of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide.. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated.. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane).. The fractions containing product were concentrated and allowed to stand.. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

According to the analysis of related databases, 193354-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a boiling slurry of 1 mmol of imidazothiazolotriazine hydrobromide 1a and 1b and 1 mmol of an appropriate isatin 2 in 15 mL of methanol, 0.108 mL of 40% water solution of KOH was added. The reaction mixture was stirred for 2 h. The precipitate separated on cooling the reaction mixture was filtered off, if necessary recrystallized from methanol, and dried.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Izmest?ev; Gazieva; Kulikov; Anikina; Kolotyrkina; Kravchenko; Russian Journal of Organic Chemistry; vol. 53; 5; (2017); p. 753 – 763; Zh. Org. Khim.; vol. 53; 5; (2017); p. 741 – 750,10;,
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Application of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-oxoindoline-6-carboxylate (4.08 g) and Mel (6.12 g) in DMF (61 ml) was added at 22 C NaH (1.71 g) over a period of 1.5 h and stirring was continued for 4 h. The mixture was partitioned between aqueous hydrochloric acid (1 M) and EtOAc, the organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane) to give the title compound (0.64 g, 13%) as a brown solid. MS (ESI, m/z): 234.5 [(M+H)+]. The second fraction contained 3,3-dimethyl-2-oxo-2,3-dihydro-lH- indole-6-carboxylic acid methyl ester (3.82 g, 82%) as brown solid. MS (ESI, m/z): 220.5 [(M+H)+].

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. .1.54 2-((2-(2-(Butan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (2C) White powder, mp 135-142 C, 87% yield; 1H NMR (400 MHz, CDCl3): delta 1.08-1.12 (t, 3H, CH3), 2.20 (s, 3H, CH3), 2.27-2.31 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.76 (bs, 2H, Ar), 7.86-7.87 (m, 2H, Ar).

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; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 19727-83-4

To an oven dried flask equipped with a stir bar cooled under argon was added 6-nitroindoline (2.0 grams, 12.2 mmol) and 61.0 mL of anhydrous drichloromethane. While stirring at 0 C 2- methoxyacetyl chloride (1.3 mL, 14.6 mmol) was added followed by triethylamine (2.2 mL, 16 mmol). The reaction slowly warmed to room temperature. Once complete, determined by LCMS, the reaction was quenched with water, and the organic material extracted using dichloromethane. The aqueous material was washed with dichloromethane twice. The combined organic material was washed with NaHC03 (sat.), brine, dried with Na2S04, filtered and concentrated. The crude material was then used without further purification.

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 19727-83-4.

Reference:
Patent; MUSC FOUNDATION FOR RESEARCH DEVELOPMENT; U.S. DEPARTMENT OF VETERANS AFFAIRS; LINDSEY, Christopher, C.; BEESON, Craig, C.; SCHNELLMANN, Rick, G.; (51 pag.)WO2018/85491; (2018); A1;,
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Application of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromoisoindolin-1-one (636 mg,3.0 mmol), 1D (800 mg, 3.0 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), Xantphos (52 mg, 0.09 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in dioxane (60 mE) was heated to 1000 C. for 4 h. After that time, the mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel (1%-10% EtOAc in pet. ether) to afford 5A (400 mg, 34%) as a yellow solid: ?H NMR (400 MHz, DMSO-d5) oe8.71 (s, 1H), 8.61 (d, J=8.4 Hz, 1H), 8.07 (t, J=8.4 Hz, 1H),8.0 (d, J=7.6 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 7.76 (d, J=3.2 Hz, 2H), 5.17 (s, 2H), 4.11-4.04 (m, 1H), 1.14-1.11 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 396.1, 398.1 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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