Category: indolines-derivatives

Related Products of 6341-92-0, 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 6341-92-0 as follows.

Is added to the reactor 153.8 mg (0.85 mmol) 6 – chloro – isatin and 102.1 mg (1.02 mmol) 2, 4 – pentanedionato, add 50 ml toluene and 5 ml DMF as the reaction solvent, adding 13.6 mg KMnO4, 7.5 Mg MnO2And 20 mg of strongly acidic ion resin D001 as catalyst, electric jacket is heated to 115 C, magnetic stirring reflux reaction for 9 hours. Thin-layer chromatographic trace to after the reaction is complete, evaporating the solvent under reduced pressure, the filter cake is toluene washing, drying to obtain the target compound 127.2 mg, total yield 56.9%.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Jia Minyi; Wang Xuechuan; Dong Hao; Wang Qiang; (12 pag.)CN108558895; (2018); A;,
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Synthetic Route of 61-70-1, 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. 61-70-1 name is 1-Methylindolin-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.

N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58% yield.1H-NMR (300MHz, CDCl3) delta(ppm) : 7.42-7.39 (d, 1H), 7.26 (s, 1H), 6.71-6.68 (d,1H), 3.52-3.20 (s, 2H), 3.19 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
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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. Application In Synthesis of 7-Fluoroisatin

This compound was prepared following the procedure of Johnson, B. L.; Rodgers, J. D. Syn. Comm. 2005, 35, 2681-2684. A suspension of 5.28 g 7-fluoroisatin in 30 mL of water was added 1.30 g NaOH, in 10 mL water with stirring. The resulting dark red solution was stirred until all of the solids dissolved and was then cooled in an ice water bath. The solution was then slowly added a cooled (ice bath) solution of 2.21 g NaNO2 in 10 mL water. These combined solutions were then added slowly to cooled (ice bath) to solution of aqueous sulfuric acid (3.4 mL H2SO4 in 60 mL water). Ice was added to maintain a temperature of approximately 0 C. After stirring for approximately 10 minutes, this dark red diazonium solution was added slowly to a chilled (0 C., ice bath) solution of 18 g SnCl22H2O in 30 mL concentrated HCl. Ice was again added to maintain a temperature of approximately 0 C. After stirring for approximately 1 hour, the reaction was filtered and the resulting residue was dissolved in 1 N NaOH (60 mL), washed with ether (2×50 mL). The resulting yellow-brown solution was cooled in an ice bath and acidified to a pH3 (litmus paper) with concentrated HCl, which resulted in the formation of a dark yellow precipitate. The precipitate was collected by filtration, washed with water, and dried over night in an oven to give 3.69 g (47%) of 7-fluoro-1H-indazole-3-carboxylic acid as an orange solid. 1H NMR (400 MHz, DMSO-d6) delta 14.35 (br s, 1H), 13.22 (br s, 1H), 7.89-7.87 (m, 1H), 7.26-7.21 (m, 2H). MS (ESI) m/z 181 (M+H)+.

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

Reference:
Patent; Pfizer Inc.; US2011/28447; (2011); 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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H8N2O2

4-(3-Chloro-2-hydroxypropylamino)-N-methylphthalimide Twenty-five grams (g) (0.142 mole) 4-amino-N-methylphthalimide [Flitsch, Chem. Ber. 94:2494(1961)] and 20.7 g (0.21 mole) 1-chloro-2,3-epoxypropane were added to 150 ml 2,2,2-trifluoroethanol and the reaction mixture was heated to reflux with stirring for 48 hours. Seventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation and a heavy yellow precipitate formed when the remaining solution cooled to room temperature. This precipitate was triturated with ethyl acetate, collected by filtration and dried to give 29.5 g (77% yield) of the desired phthalimide intermediate m.p. 136-138.5 C. Analysis: Calculated for C12 H13 ClN2 O3: C, 53.64; H, 4.88; N, 10.45. Found: C, 53.87; H, 4.85; N, 10.81.

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; Miles Laboratories, Inc.; US4261893; (1981); A;,
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Application of 20780-77-2, 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. 20780-77-2, name is 6-Iodoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

c. 7-Iodo-2H-3,1-benzoxazine-2,4(1H)-dione To a stirred warm (80 C.) solution of 6-iodo-1H-indole-2,3dione (3.0 g, 11 mM) in acetic acid (10 mL) and acetic anhydride (10 mL) was added in small portions chromium trioxide (1.83 g, 18.3 mM) while maintaining the temperature of the reaction mixture at 80-90 C. The reaction mixture was then heated at 80 C. for 10 min, cooled and poured into water. The resulting mixture was filtered and the collected solids dried to provide the title compound as a yellow solid (2.6 g, 81.8%); MS(CI): 290 (M+H).

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-Iodoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
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Reference of 20870-79-5, These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-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.

(c) Preparation of 5-Amino-2-oxindole. The 5-nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Safety of 6-Bromoisoindolin-1-one

6-(5-Hydroxy-pent-1 -ynyl)-2,3-dihydro-isoindolin-1 -oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (40 g, 0.18 mol), bis(triphenylphosphine) palladium dichloride (6.6 g, 0.009 mol), CuI (3.57 g, 0.01 mol) and Et3N 5 (930 mL) in dry DMF (930 mL) was slowly added 4-pentyn-1-ol (33.2 mL, 0.37 mol). The reaction mixture was bubbled with argon for 20 min and heated at 100 “C for 24 h. The solvent in the reaction mixture was evaporated and the crude residue was washed with DCM(100 mL), filtered and dried to give e-^-Hydroxy-pent-i-ynyl^.S-dihydro-isoindolin-i-one as a black solid (25 g, 61%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H, s), 7.5-7.6 (2H, d), 7.5 0 (1H, S), 4.5 (1H, t), 4.3 (2H, s), 3.5 (2H, s), 2.4-2.5 (2H, s), 1.6 (2H, q); MS: AP: M+1: 216(215).

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; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

Weigh rapamycin (0.05mmol), isatin 3k (0.10mmol) and rhodium octanoate dimer(0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary evaporation to give a crude product. The rapamycin analog I-k was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 79percent.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-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 13861-75-1, Recommanded Product: 13861-75-1

A. Preparation of 5′-(1-oxopropyl)spiro-[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one A slurry was made from 7.5 ml of dimethylformamide and 45.5 g of anhydrous aluminum chloride. The temperature rose to 40 C. and 2.97 ml of propionyl chloride and 5.43 g of spiro[cyclopropane-1,3′-[3H]-indol]-2′(1’H)-one were added. The mixture was stirred for 2 hours at 70 C. and was slowly poured into a mixture of ice and 50 ml of concentrated hydrochloric acid. After cooling overnight, the resulting precipitate was recovered by filtration. Crystallization from ethyl acetate provided 4.9 grams of the desired subtitle intermediate, m.p. 183-185 C. Analysis for C13 H13 NO2: Calculated: C, 72.54; H, 6.09; N, 6.51; Found: C, 72.47; H, 6.14; N, 6.42.

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; Eli Lilly and Company; US4617302; (1986); A;,
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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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromoisoindolin-1-one

Step 1: 5-(Ethylthio)isoindolin-1-one (0428) (0429) 5-Bromoisoindolin-1-one (10 g, 47.16 mmol) and sodium ethanethiolate (9.92 g, 117.90 mmol) were mixed together in DMF (100 mL) and the reaction heated to 100 C. for 20 min. The reaction was cooled to room temperature, poured into water (100 mL) and the product extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine (4×50 mL). LCMS indicated product in the aqueous washings consequently they were combined and extracted with EtOAc (4×50 mL). The organic extracts were combined, dried using a phase separator cartridge and concentrated in vacuo. The solid obtained was dried under high vacuum overnight. 5-(Ethylthio)isoindolin-1-one (8.68 g, 95%) was obtained as a yellow solid. The material was used in the next step without further purification. (0430) LC/MS: m/z=194 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 1.27 (t, 3H), 3.06 (q, 2H), 4.33 (s, 2H), 7.36 (dd, 1H), 7.47-7.48 (m, 1H), 7.57 (d, 1H), 8.45 (s, 1H).

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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