Month: March 2021

Electric Literature of 193354-13-1,Some common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, molecular formula is C8H6INO, 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.

Step 1. Synthesis of 5-Methoxycarbonyl-2-oxindole. 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.15 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 a silica gel in 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.

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-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 32692-19-6, Computed Properties of C8H8N2O2

General procedure: A solution of indoline (20) (1.88 mL, 16.78 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (22) (3.73 g, 20.13 mmol) in dry methanol (20 mL) was treated with AcOH (2.37 mL, 41.95 mmol) followed by NaCNBH3 (1.26 g, 20.13 mmol) at 0 C. ;The reaction was brought to room temperature and stirred for 3 h. ;The reaction was basified with 1 N NaOH solution and product was extracted into CH2Cl2. ;The combined CH2Cl2 layer was dried (Na2SO4) and solvent was evaporated to obtain crude product. ;The crude was purified by column chromatography (EtOAc:hexanes, 1:9) to obtain the title compound

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; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 317-20-4

General procedure: The mixture of isatin 1 (58.9 mg, 0.4 mmol), antipyrine 2 (37.6 mg, 0.2 mmol) andimidazole (20 mol %, 0.04 mmol) in 1 mL H2O were stirred at 80 . Once thereaction completed, the solid mixture was filtered, washed by water and dried undervacuum to afford the analytically pure products 3. In some cases, the desired pureproducts were obtained by silica gel chromatography using ethyl acetate as eluent.

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

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1504-06-9, name is 3-Methyloxindole, 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. SDS of cas: 1504-06-9

A magnetic stirrer was added to the Schlenk tube-sealed reactor, and the 2- oxindole compound of formula II-1 (0.3 mmol) was added, followed by the addition of Cu (OAc) 2 (0.03 mmol) and di-tert-butyl peroxide. (0.6mmol); The reactor was then placed in an oil bath equipped with magnetic stirring, and the reaction was heated and stirred at 120 C for 4 hours. The reaction mixture was completely monitored by TLC. After the completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue was separated by column chromatography (eluent solvent: ethyl acetate / n-hexane) to obtain he title compound formula I-1 , yield 80%.

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (11 pag.)CN108129378; (2018); A;,
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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, A new synthetic method of this compound is introduced below., name: 1-(2,6-Dichlorophenyl)-2-indolinone

Example 1Step a) of preparation of sodium diclofenacIn a four-necked glass flask the following ingredients were charged:- 1 -(2,6-dichlorophenyl)-2-indolinone g 592 (M.W. 278.13 moles: 2.128)- Water cc 2368- Sodium hydrosulfite g 40- Sodium hydroxide 30 % g 851 (M.W.: 40; moles: 6.38)The mixture was refluxed for 6 hours, then cooled to 35 – 37 C. The precipitate was filtered on buchner funnel, then washed with water (cc 1600) preheated to 35- 37 C. Wet 1016 grams of sodium diclofenac were obtained corresponding to dry 625 grams (Theor. g 677.1 )

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; COSMA S.P.A.; IBSA INSTITUT BIOCHIMIQUE S.A.; AVOGADRI, Alvaro; LUSSANA, Massimiliano; PIZZATTI, Enrica; BARETTI, Sergio; WO2010/69397; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, 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 1504-06-9, category: indolines-derivatives

Step 1 : Preparation of 3-methyl-5-(3-trifluoromethylphenyl)- 1 ,3-dihydroindol-2-oneA solution of 3-methyloxindole (5.06 g, 34.4 mmol) in iV,iV-dimethylformamide (60 mL) was cooled to 0 0C. N-Bromosuccinimide (6.23 g, 35.0 mmol) was added, and the resulting solution was stirred for 18 hours while slowly warming to room temperature. The reaction was then diluted with ethyl acetate (100 mL) and washed with 1 :1 saturated aqueous NaCl solutuion:H2O (3 x 75 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid that was used without further purification in the next step described below.A mixture of the crude product described above (1.02 g5 4.51 mmol), 3- (trifluoromethyl)phenylboronic acid (0.983 g, 5.18 mmol), sodium carbonate (0.884 g, 8.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.252 g, 0.218 mmol) in ethylene glyclol dimethyl ether (8.0 mL) and H2O (1.0 mL) was warmed to 80 0C. After 20 hours, the mixture was cooled to room temperature, poured into 1 : 1 saturated aqueous NaCl solution:H2O (50 mL), and extracted with ethyl acetate (3 x 50 mL). The organic extracts were combined, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 10-35% ethyl acetate/hexanes, to give 3-methyl-5-(3-trifluoromethylphenyl)-l,3-dihydroindol-2-one as a white solid.1H NMR (CDCl3): delta 8.27 (br s, 1 H), 7.79 (s, 1 H), 7.72 (d, I H1 J = 7.3 Hz), 7.56 (m, 2 H), 7.46 (m, 2 H), 6.99 (m, 1 H), 3.55 (dd, 1 H, J = 15.3, 7.8 Hz), 1.57 (d, 3 H, J = 7.7 Hz) MS: m/e 292.41 (M + H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 suspension of tert-butyl 5-bromo-2-(tert-butoxycarbonyl)isoindoline (1.2 g, 4 mmol) and bis(pinacolato)diboron (2 g, 8 mmol) in DMSO (20 mL) was added AcOK (1.6 g, 16 mmol), followed by Pd(dppf)Cl2-CH2Cl2 (327 mg, 0.4 mmol) under N2 atmosphere. The reaction was heated at 90 C for 12 h, then cooled to rt and poured into EtOAc/H20 (300 mL/100 mL). The separatedorganic phase was washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) =20/1) to give the title compound as yellow oil (1 g, 73%). MS (ESI, pos. ion) m/z: 290.2 [M-56+l ; NMR (400 MHz, CDC13) delta (ppm): 7.68-7.74 (m, 2H), 7.23-7.30 (m, 1H), 4.64-4.70 (m, 4H), 1.53 (s, 9H), 1.36 (s, 12H).

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

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-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 18711-13-2, Computed Properties of C8H3Cl2NO2

General procedure: To a stirred solution of ethyl 2-(triphenylphosphoranylidene)acetate (3.83 g, 11.0 mmol) in CH2Cl2 (30.0 mL) was added isatin (1.47 g, 10.0 mmol) at 0 C. After stirring for 8 h at 0 C, the mixture was concentrated by rotary evaporation. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=3:1-10:1) to afford the compound 1a as a red solid (1.78 g, 82 %).

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; Zhao, Jia; Guan, Shuicheng; Zhou, Xiaojian; Han, Wenyong; Cui, Baodong; Chen, Yongzheng; Tetrahedron; vol. 72; 22; (2016); p. 3098 – 3104;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 64483-69-8

PREPARATION V 1-(N-Benzoylcarbamoyl)-5-acetyloxindole To 3.0 g. (.017 mole) of 5-acetyloxindole in 75 ml. of xylene and 25 ml. of toluene was added 3.3 g. (.022 mole) of benzoylisocyanate, and the reaction mixture heated to reflux overnight. The hot suspension was filtered, washed with toluene and air dried, 4.4 g., m.p. 232C. dec.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; EP208510; (1991); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-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. Recommanded Product: 2-Methylisoindoline-1,3-dione

General procedure: To N-methylphthalimide (1a) (8 mmol), N-benzylphthalimide (1e) (8 mmol) or appropriate compound 2b-d(8 mmol) stirred in acetic acid (25 mL) tin granular (1.90 g, 16 mmol) and hydrochloric acid (10 mL, d25 = 1.2 g/mL) were added. The whole lotwas heated to reflux for 3 h. The solvents were removed under reduced pressure and to the residue were added ethyl acetate (50 mL) and sodium carbonate solution(10% in water) to obtain an alkaline environment. Then the organic layer was separated, washed with water, dried with magnesium sulfate(VI) and evaporated to give the crude products 3. Thecompounds 3 were purified by crystallization.

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

Reference:
Article; Jo?wiak, Andrzej; Zagorski, Piotr M.; P?otka, Mieczys?aw W.; Cal, Dariusz; Tetrahedron Letters; vol. 55; 15; (2014); p. 2420 – 2422;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem