Tag: M.W=200-300

Reference of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

EXAMPLE 3 2 moles of Piperazine Benzisothiazole hydrochloride, 1 mole of 5-(2-chloroethyl)-6-chlorooxindole in water (20 times based on benzisothiazole) and in the presence of dispersing agent. All the reactants are charged in to the flask and refluxed under nitrogen, under stirring for 12-16 hr. After the completion of the reaction, the reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried in IPA and then in water and isolated by filtration. The solid is dried at 95-100 C.Yield: 90-92%, Purity 98% (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; ALKEM LABORATORIES LIMITED; US2011/3995; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 337536-15-9, 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. 337536-15-9, name is 4-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

Example 10 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0572] In four parallel procedures, four portions of 175 mg (0.42 mmol) of the product from step 3 are each dissolved in 5 ml dioxane and combined with 128 mg (0.50 mmol) of bis-pinakolato-diboron, 123 mg (1.26 mmol) potassium acetate and 21 mg (0.025 mmol) [1,1-bis-(diphenyl-phosphino)ferrocene]-dichloropalladium-dichloro-methane complex. Each reaction mixture is stirred in the microwave for 1 h at 120 C., cooled to RT, combined with 85 mg (0.50 mmol) of the compound from example 22A, 0.42 ml (2 N in water, 0.84 mmol) of a sodium carbonate solution and 17 mg (0.02 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium-dichloromethane complex and stirred for 2 h at 120 C. The reaction mixtures are combined. The suspension is diluted with acetonitrile, filtered through a Millipore filter and separated by preparative HPLC (solvent: acetonitrile/water gradient). Once the resulting solid has crystallized out of the acetonitrile, this produces 286 mg (36% of theoretical yield) of the title compound. Example 11 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-isoindole-1-one [0575] [0576] The synthesis of the title compound is performed starting from 100 mg (0.24 mmol) of the product from step 3 of the compound from example 10 in a manner analogous to step 4 of the synthesis of the compound from example 10. Instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (61 mg, 0.29 mmol) is used. This produces 28 mg (24% of theoretical yield, 94% purity) of the title compound. [0577] 1H-NMR (400 MHz, DMSO-d6): delta=4.73 (s, 2H), 7.21 (s, 1H), 7.51-7.60 (m, 2H), 7.61-7.69 (m, 3H), 7.72 (d, 1H), 7.89 (d, 1H), 8.17 (d, 1H), 8.61-8.71 (m, 2H), 8.75 (s, 1H). [0578] LC-MS (Method 3): Rt=1.13 min; MS (ESIpos): m/z=471 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

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; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 118289-55-7, The chemical industry reduces the impact on the environment during synthesis 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, I believe this compound will play a more active role in future production and life.

Example 15 5-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride A mixture of 6-chloro-5-(2-chloroethyl)indolin-2-one (332 mg, 1.45 mmol), the product of Reference Example 1 (370 mg, 1.45 mmol), sodium carbonate (461 mg, 4.35 mmol), iodine sodium (216 mg, 1.45 mmol) and water (5 ml) was stirred under reflux for 24 hours. The reaction was cooled to room temperature, extracted with methylene chloride and water. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and subjected to column chromatography to obtain an oil. Hydrogen chloride-ethanol solution was added thereto under stirring, the resulting salt was slurried in isopropanol, filtered to give a pale yellow solid (308 mg, yield: 51%). 1HNMR (400 MHz, DMSO-d6): delta ppm 11.04 (brs, 1H), 10.55 (s, 1H), 7.77 (d, 1H), 7.71 (d, 1H), 7.50 (d, 1H), 7.32 (t, 1H), 7.29 (s, 1H), 6.98 (d, 1H), 6.88 (s, 1H), 3.71 (d, 2H), 3.57 (d, 2H), 3.50 (s, 2H), 3.38 (m, 4H), 3.21 (m, 4H). ESI-MS (m/z): 412.2 [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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

1-2: Dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)malonate; 3.5 g (87 mmol) of sodium hydride are added portionwise to a solution of 25 g (87 mmol) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)malonate in 250 ml of tetrahydrofuran cooled to 2 C. The reaction medium is stirred at ambient temperature for 30 minutes and then brought back to 2 C., before adding, dropwise, 21 g (87 mmol) of 2-bromomethylisoindole-1,3-dione in 200 ml of tetrahydrofuran. The reaction medium is stirred at ambient temperature for 20 h, treated by adding 500 ml of water and then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, and concentrated under vacuum.The crude product obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)malonate are obtained in the form of a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; US2012/323006; (2012); A1;,
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 18711-13-2 as follows. Product Details of 18711-13-2

General procedure: Sulfonated-beta-cyclodextrin (beta-CD-SO3H) (76 mg, 0.06 mmol) was dissolved in water (5 mL) at RT by stirring to get the clear solution in 50 mL round bottom ask. Further, isatin 2 (0.31 mmol) and tryptamine 1a/isotryptamine 1b (0.31 mmol) were added to the solution under constant stirring and mixture was heated at 80 C for 8-12 h. The progress of the reaction was monitored by TLC. After completion of reaction, it was cooled to room temperature, water was added to it. The aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product obtained was puried by column chromatography using chloroform/methanol (99:1) as an eluent furnishing the product. The spectral and analytical data of all the reported products is consistent with the previous (6c,d,f) reports.

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Urmode, Tukaram D.; Dawange, Monali A.; Shinde, Vaishali S.; Kusurkar, Radhika S.; Tetrahedron; vol. 73; 30; (2017); p. 4348 – 4354;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-15-4, name is 4,6-Dichloroisatin, 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 18711-15-4, HPLC of Formula: C8H3Cl2NO2

a. 5,7-Dichloro-2H-3,1-benzoxazine-2,4(1H)-dione To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80 C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80-90 C. during the addition of the chromium trioxide. After the addition was complete, the reaction mixture was diluted with water (100 mL) and then filtered to separate the precipitated solids. The solids were washed thoroughly with water and then dried to obtain the title compound as a yellow solid (4.13 g, 72%); MS(CI): 232 (M+H).

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; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-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. name: 6-Bromoisoindolin-1-one

6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (3Og, 0.14mole), bis (triphenylphosphine) palladium dichloride (5 g, 0.007 mole), CuI (2.6 g, 0.01 mole), dry Et3N (700 mL) in dry DMF (700 mL) was added 3-butyn-1-ol (21.3 mL, 0.28 mole) slowly drop- wise. The reaction mixture was bubbled with argon for 20 min and heated at 100 C for 24 h. The solvent was evaporated and the crude residue was washed with DCM (100 mL), filtered and dried to 6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-one as a pale grey solid (24 g, 85%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H1 s), 7.5-7.6 (2H, d), 7.5 (1H,s), 4.9 (1H, t), 4.3 (2H1 s), 3.6-3.7 (2H, t), 2.4-2.6 (2H, t); MS: M+1: 202 (201)

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 423116-18-1, 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. 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-tert-Butyl-11-phthalimidomethyl-7,14,15-trioxadispiro[5.1.5.2]pentadecane (OZ384). A solution of O-methyl 4-tert-butylcyclohexanone oxime (2.74 g, 15 mmol) and 4-phthalimidomethylcyclohexanone (2.57 g, 10 mmol) in cyclohexane (100 ml) and CH2Cl2 (100 ml) was treated with ozone according to the general procedure. The reaction mixture was concentrated, triturated with ethanol (50 ml), and filtered. The cake was purified by flash chromatography (silica gel, 10% EtOAc in hexanes) to afford trioxolane OZ384 (0.41 g, 10%) as a colorless solid. mp 175 C. dec; 1H NMR (500 MHz, CDCl3) delta0.86 (s, 9H), 0.94-1.05 (m, 1H), 1.21-1.42 (m, 4H), 1.47-2.02 (m, 13H), 3.56 (d, J=7.3 Hz, 2H), 7.70-7.74 (m, 2H), 7.81-7.87 (m, 2H); 13C NMR (125.7 MHz, CDCl3) delta24.50, 27.66, 27.81, 32.29, 33.43, 34.54, 35.59, 43.10, 47.23, 108.74, 108.89, 123.24, 132.00, 133.92, 168.53. Anal. Calcd for C25H33NO5: C, 70.23; H, 7.78; N, 3.28. Found: C, 70.46; H, 7.90; N, 3.43.

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, 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICINES FOR MALARIA VENTURE MMV; US2005/256185; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20780-77-2, 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. 20780-77-2 name is 6-Iodoindoline-2,3-dione, 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.

Method IAccording to this method Examples 1-14 and 22-24 were prepared. The indirubin derivatives are prepared according to Russel G. A., Kaupp G. (1969), J. Am. Chem. Soc., 91, pages 3851-3859. ; Example 1 6-iodo-indirubinYield: 68%, fine deep-purple powderCHN-analysis: C16H9IN2O2 (MW: 388.16 g/mol) calc.: 49.5%; C, 2.3%; H, 7.2%; N. found: 49.3%; C, 2.1%; H, 7.1%; N.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Faustus Forschungs Cie. Translational Cancer Research GmbH; US6987092; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem