Tag: M.W=100-200

Synthetic Route of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Part 1: tert-Butyl 2-oxo-2,3-dihydro-1H-indol-5-ylcarbamate (21): To a mixture of 5-amino-1,3-dihydro-2H-indol-2-one (148 mg, 11.0 mmol), di-tert-butyl dicarbonate (262 mg, 1.2 mmol), and Et3N (279 muL, 2.0 mmol) was added dry THF (5 mL). The suspension was then stirred at rt for 24 h. The reaction was concentrated in vacuo to yield tert-butyl 2-oxo-2,3-dihydro-1H-indol-5-ylcarbamate as a brown solid. 1H NMR (CDCl3, 400 MHz): delta 1.52 (s, 9H), 3.52 (s, 2H), 6.38 (brs, 1H), 6.76 (d, J=8.0 Hz, 1H), 7.07 (dd, J=2.4, 8.4 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.42 (brs, 1H). MS (ES+): m/z 249 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Aminoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, An-Hu; Dong, Hanqing; Zhang, Tao; US2006/63791; (2006); A1;,
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Application of 39755-95-8, 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 39755-95-8 as follows.

Synthesis of 5-methoxyoxindole; [0095] To a solution of 5-methoxyisatin ( 10.62 g, 60 mmol) in DMSO (30 mL) was added N2H4 xH20 (hydrazine hydrate, 6 mL, 120 mmol) dropwise over 5 min (exothermic). After addition, the resulting mixture was heated at 140 C (oil temp.) for 2h and then cooled to rt. After diluting with H20 (30 mL), 6 M HC1 (12 mL, 72 mmol) was added and the resulting mixture was stirred for lh at rt. Ice (30 mL) was added and the reaction mixture was stirred O/N at rt. The precipitate formed was collected by suction filtration, rinsed with H20, then dried to give the 5-methoxyoxindole (6.523 g) as a brown solid, (about 10% impurity being the oxime from starting material 5-methoxyisatin) NMR (400 MHz, d6- DMSO) 6.78 (s, 1H), 6.85 (s, 1 H), 6.72-6.79 (m, 2H), 3.39 (s, 3H); ESI 164.0 [M + H]+, calcd for [C9H9N02 + H]+ 164.1.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
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317-20-4, name is 7-Fluoroisatin, 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. name: 7-Fluoroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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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. 61-70-1, name is 1-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylindolin-2-one

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

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 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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Reference of 13861-75-1, 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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, This compound has unique chemical properties. The synthetic route is as follows.

A dried flask under nitrogen was charged with sodium hydride (120 mg, 3.0 mmol) and DMF (1 mL). This rapidly stirred suspension was cooled to 0C using an ice/water bath and spiro[cyclopropane-l,3′-indolin]-2′-one (160 mg, 1.0 mmol, Preparatory Example 4) was added dropwise as a solution in DMF (2 mL). The ice/water bath was removed for 1 minutes before the mixture was recooled to 0C and 2-(chloromethyl)-l- isopentyl-lH-benzo[JJimidazole hydrochloride (236 mg, 1.0 mmol) was added dropwise as a solution in DMF (2.1 mL). The mixture was allowed to warm to rt and stirred there for 16 hours.The mixture was cooled to 0C and ice was added carefully. Partition between EtOAc and water was followed by separation, drying and concentration in vacuo. Preparative HPLC gave isolation of the desired compound, (1 10 mg, 0.31 mmol, 31%). ? NMR (400 MHz): ? 0.96 (d, 6H), 1.45 ( m, 2H), 1.60 (m, 2H), 1.69 (m, IH), 1.82(m, 2H), 4.26 (m, 2H), 5.35 (s, 2H), 6.83 (d, IH), 7.02 (dd, IH), 7.19 (dd, IH), 7.29 (m, 3H), 7.47 (d, IH), 7.81 (m, IH). LC/MS 360 (MH+).

The chemical industry reduces the impact on the environment during synthesis Spiro[cyclopropane-1,3′-indolin]-2′-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; PILKINGTON, Christopher; LUMLEY, James; ANGELL, Richard; MATHEWS, Neil; WO2013/68769; (2013); A1;,
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These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 Potassium 1,3-dioxoisoindolin-2-ide

o a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).1H NMR (400 MHz, CDC13): delta 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

The synthetic route of Potassium 1,3-dioxoisoindolin-2-ide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (244 pag.)WO2018/98208; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110568-64-4, name is 6-Nitroisoindolin-1-one, belongs to indolines-derivatives compound, 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 110568-64-4, Formula: C8H6N2O3

A mixture of 5-nitro-1 lead noise isobutyl ketone Jie (100mg, 0.56mmoL), reduced iron powder (314mg, 5.6mmoL) was added to ethanol (2. OmL) and concentrated hydrochloric acid (0.5mL) and heated under reflux for 2 hours , TLC the reaction was complete. Cooling, the methanol solution saturated with ammonia (NH3) neutralizing the acid, diatomaceous earth filtration, washed with methanol, the solvent evaporated under reduced pressure to give a white solid 70.0mg, 84% yield

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; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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Application of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(1, 3-dioxoisoindolin-2-yl) acetaldehyde (4.0 g, 21.15 mmol) in ethanol (40 mL) added hydroxylamine. HC1 (2.930 g, 42.305 mmol), followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at roomtemperature for 16 h. Evaporated off the solvent, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL), followed by brine , dried over sodium sulfate and concentrated under vaccue to give the titled compound (3.2 g, 74percent) as off white solid. LCMS: m/z 204.1 [M+H] ?H NMR (300 MHz, DMSO-d6) 11.36 (s, 1H), 7.98?7.78 (m, 4H), 6.83 (t, J= 3.8 Hz,1H), 4.39 (dd, J= 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1074-82-4

(k) Preparation of 3-phthalimidylpropanol (compound 106) 3-Bromopropanol (4.0 g, 28.78 mmol), potassium phthalimide (8.0 g, 43.17 mmol) and potassium carbonate (4.0 g, 28.78 mmol) were added to 20 mL DMF. The reaction mixture was stirred at 70 C. for 4 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, saturated NaCl solution and evaporated in vacuo to a solid which was crystallized in ethyl acetate (3.5 g, 67%).

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 1074-82-4.

Reference:
Patent; CytoMed Incorporated; US6201016; (2001); B1;; ; Patent; Cytomed, Inc.; US5681966; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, belongs to indolines-derivatives compound, 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 39603-24-2, Computed Properties of C10H9NO2

General procedure: To a solution of isatin 1 (0.5 mmol) in THF (2 mL) was added quinine (0.017 g, 10 mol%). The mixture was cooled to -78 C and stirred at this temperature for 15 minutes. Then the solution of 2-(trimethylsilyloxy)furan 2 (0.156 g, 1 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 C for 15 minutes. The reaction was monitored by TLC. After the completion ofthe reaction it was quenched by addition of 10% aqueous HCl (2.0 mL) and the mixture wasextracted with ethyl acetate (3¡Á5 mL). The combined organic layer was washed with brine solution,dried over MgSO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (AcOEt/hexane) to afford the product as a white solid.

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:
Article; Kong, Shasha; Fan, Weidong; Lyu, Hairong; Zhan, Junchen; Miao, Xinyu; Miao, Zhiwei; Synthetic Communications; vol. 44; 7; (2014); p. 936 – 942;,
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