Tag: M.W=100-200

Electric Literature of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

[0195] To 2,3-dihydro-isoindol-l-one (250.Omg, 1.85mmol) in acetonitrile (9mL) was added propargyl bromide (308.6uL, 2.77mmol) and cesium carbonate (2.4g, 7.39mmol) and the mixture was allowed to stir at 80C for two hours. An aqueous workup was done to provide the title compound (303.3mg, 96%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-Nitroindoline, 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 19727-83-4, Recommanded Product: 6-Nitroindoline

At room temperature, 6-nitroindoline (99 mg, 0.6 mmol) was added to the reaction tube containing p-methylthiophenol (62 mg, 0.5 mmol) and dimethyl sulfoxide (1.0 mL). After stirring uniformly at room temperature, riboflavin 1 (0.025 mmol, 8 mg) and elemental iodine (0.05 mmol, 13 mg) were added in sequence, and then vacuum oxygen protection was applied. After the reaction tube was reacted at 60C for 24 hours, it was cooled to room temperature, and saturated sodium thiosulfate solution was added to quench the reaction. Then, the reaction solution was extracted with ethyl acetate, and then washed with saturated sodium chloride solution, and the organic layers were combined and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation.Finally, it was purified by column chromatography (n-hexane: ethyl acetate = 30: 1) to obtain a yellow solid 6-nitro-3-(4-methylphenylthio)indole 106 mg, yield 75%.

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; Zhejiang University of Technology; Jiang Xinpeng; Zhao Zongchen; Yu Chuanming; (8 pag.)CN111100056; (2020); A;,
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. 324-03-8, name is 6-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 324-03-8

General procedure: A 25-mL flask, equipped with a magnetic stirring bar, was charged with 2-(1,3-dithiolan-2- ylidene)acetonitrile 1a (143 mg, 1.0 mmol), isatin 2a (74 mg, 0.5 mmol), and MeCN (3.0 mL), followed by addition of a solution of I2 (25 mg, 0.1 mmol) in MeCN (1.0 mL). The reaction mixture was stirred at 80 C for 12 h. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (1.0 mL) and water (20.0 mL), and stirred for another 10 min. The fully precipitated solid was filtered and washed with water (20.0 mL). Then it was further washed with petroleum ether-ethyl acetate (1/1, V/V, 20.0 mL) and dried under vacuum to afford 3a.

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Deqiang; Li, Xiangguang; Yang, Juan; Li, Yanni; Wang, Baoling; Cheng, Ping; Synthetic Communications; vol. 46; 23; (2016); p. 1924 – 1931;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 7477-63-6 as follows. COA of Formula: C8H4ClNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 ¡ãC (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-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 611-09-6, COA of Formula: C8H4N2O4

A mixture of 5-nitroisatin 22a (5.0 g, 26.0 mmol), 2, 2′-dimethylpropane-1, 3-diol (2.69 g, 25.9 mmol) and a catalytic amount ofp-TSA was suspended in cyclohexane (35 mL) and refluxed with azeotropic removal of water using Dean-Stark apparatus, overnight. The reaction mixture was cooled to room temperature and the solid that separeted was filtered, washed with dilute aqueous sodium bicarbonate, water and then air dried to give 22b. Yield 6. 5g, 90%.

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

Reference:
Patent; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Recommanded Product: Isoindoline

Under N2, at 0 0C, trichloroacetyl chloride (0.57 mL, 5.0 mmol) was added dropwise to a stirring solution of isoindoline (1.0 g, 5.0 mmol), Et3N (0.7 mL, 0.51 g, 5.0 mmol) and CH2Cl2 (20 mL). The solution was allowed to warm to room temperature and stirred for 1 h. After evaporating the solvents in vacuo, the mixture was purified via silica EPO gel chromatography using 8:2 hexanes/EtOAc to obtain the desired amide (1.2 g, 4.6 mmol, 91% yield). LC/MS (10-99% CH3CN), M/Z: M+l obs = 265.9; tR = 3.51 min.

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; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/122014; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, molecular formula is C8H3ClFNO2, 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 4-Chloro-5-fluoroindoline-2,3-dione

2.00 g of 4-chloro-5-fluoroindole quinone was placed in 100 ml three-necked flask, 40 ml of toluene and 1.08 g of potassium borohydride were added in portions. The reaction was as follows: stirring and refluxing, reaction time: 5. Oh , The reaction temperature: 40 C, after the completion of the reaction, the solvent was removed by rotary evaporation to give 0.93 g of crude product of purple solid 4-C1-5-F-4 ‘-Cl-5’ -F-indirubin, The Ethanol was recrystallized to give a purple solid product, m.p.> 30 (TC (thermometer untreated).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84378-94-9, its application will become more common.

Reference:
Patent; Northwest University; Wang, Culing; Liu, Jianli; Zhao, Danqing; Liu, Zhulan; Zhang, Ning; (10 pag.)CN103980182; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylindolin-2-one, its application will become more common.

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6N2O3

5-Amino-2,3-dihydroisoindol-l-oneH2N; [693] Iron powder (158mg, 2.83mmol), water (61uL), and HC1 (37percent, 5uL,0.566mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-l-one (50.4mg,0.283mmol) in EtOH (754|^L). The above mixture was heated at 95¡ãC for 2h. After thattime, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid wasfiltered off. The filtrate was concentrated in vacua to obtain a light-yellow solid that waspurified by preparative TLC eluting with 10percent MeOH/CH2Cl2 to give a light-yellow solid of5-amino-2,3-dihydroisoindol-l-one. ‘HNMR (CD3OD, 400 MHz): 5 = 7.48 (s, 1 H), 8.08 (s,2 H), 9.91 (s, 1 H), 10.66 (d, 1 H, J= 8.8 Hz). MS (ES+): m/z 149.21 (100) [MH1″]. HPLC: *R= 1.20 min (ZQ2000, polar_5 min).

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; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 247564-59-6, name is 5,7-Difluoroindolin-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 247564-59-6, Product Details of 247564-59-6

Step 1:; 5,7-Difluorooxindole (prepared in a manner analogous to Example 62, steps 1-4 using 2,4,6-trifluoronitrobenzene instead of 2,6-difluoronitrobenzene) (0.64 g, 3.2 mmol) was dissolved in N,N-dimethylformamide (3 mL) and sodium hydride (0.24 g, 6.4 mmol, 60% wt suspension in mineral oil) was added in portions over 15 minutes and the mixture was stirred an additional 30 minutes. In a separate flask, [(2R,3R)-3-(3-fluorophenyl)oxiran-2-yl]methanol (1.08 g, 6.4 mmol, from Example 25 Step 3) was dissolved in N,N-dimethylformamide (3 mL) and titanium isopropoxide (1.89 mL, 6.4 mmol) was added and the mixture was stirred 30 minutes. The titanium isopropoxide/epoxide solution was then added to the solution of oxindole sodium salt dropwise and the mixture was stirred at room temperature for 24 hours. The mixture was then carefully quenched with 2 N aqueous hydrochloric acid and diluted with 200 mL of 2 N aqueous hydrochloric acid (use of hydrochloric acid is essential to prevent precipitation of titanium salts and subsequent emulsification). The mixture was extracted with ethyl acetate, the organic layers combined, washed with water, and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified via Isco chromatography (Redisep, silica, gradient 20% to 100% ethyl acetate in hexane) to afford 1.02 g (87%) of 5,7-difluoro-1-[(1S,2S)-1-(3-fluorophenyl)-2,3-dihydroxypropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a sticky oil. MS (ES) m/z 365.12 (M+).

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; Wyeth; US2007/72897; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem