Tag: M.W=100-200

Application of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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These common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-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. COA of Formula: C9H6ClNO2

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 mol%) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

The synthetic route of 5-Chloro-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, category: indolines-derivatives

Step 10b, Example 25b: (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 71 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 38 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.24 ml of pyridine, and then 57 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one (62 mg) is isolated in the form of a pulverulent solid (yield=63%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=-22 C.=0.351 mg/0.5 ml in DMSO

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
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Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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.

Description 12:(Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-5-methoxyindolin-2-one5-Methoxyindolin-2-one (50 mg, 0.31 mmol) and 3,5-dimethyl-W-pyrrole-2- carboxaldehyde (1.2 equiv., 45 mg) were heated together in ethanol (1 ml) and piperidine (2 drops) in a microwave (150C, 30 min). The reaction mixture was cooled to room temperature and diluted with ethanol. The precipitate was filtered, washed with ethanol, and then with ethyl ether, air-dried to give the product as an orange crystalline solid. The results set out below indicate the final product was the title compound 012.1H NMR (dmso-d6): 13.45 (1H, NH, br s), 10.58 (1H, NH, br s), 7.57 (1H, s), 7.40 (1H, s), 6.75 (1H, d), 6.65 (2H, d), 6.00 (1H, s), 3.77 (3H, s), 2.31 (6H, s).13C NMR (CDC ): 169.9, 155.5, 137.0, 32.7, 131.0, 127.6, 127.0, 123.6, 112.7, 112.0, 111.2, 109.5, 103.7, 56.0, 13.9, 11.7.MS: MH+ 269.0

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

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); 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. 3484-35-3, name is 5-Methylindolin-2-one, A new synthetic method of this compound is introduced below., name: 5-Methylindolin-2-one

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3¡¤Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

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; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5, 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

10 parts of 4-aminophthalimide and 11 parts of cyanuric chloride were added to 100 parts of nitrobenzene, and the mixture was heated at 100 to 110 C. for 5 hours. After cooling it was filtered and washed with methanol and water. And dried at 80 C. to obtain 17 parts of the intermediate (2) represented by the formula (2).

The synthetic route of 5-Aminoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainichiseika Color & Chemicals Mfg. Co., Ltd.; Iguchi, Kazunori; Yanagimoto, Hiromitsu; (18 pag.)JP5823432; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1504-06-9, 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. 1504-06-9 name is 3-Methyloxindole, 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.

3-methylindolin-2-one (441 mg, 3 mmol) in acetonitrile (5 mL) was cooled to 15C. NBS (534 mg,3 mmol) was added. After stirring for 1 h, the reaction was diluted with water (10 mL) and extractedwith EtOAc (20 mL) for three times. The combined organic phase was washed with brine, dried overNa2SO4 and concentrated under reduced pressure to give a residue which was purified by silica gelcolumn chromatography to afford compound 1b (454 mg, 67%) as a white solid.

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:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 6-Methoxyindoline-2,3-dione

General procedure: Similar to as described in General Procedure Z, 6-methoxy-2,3-dihydro- 1H-indole-2,3-dione was converted to the title compound as a yellow solid (600 mg, 10%). LC-MS (ES, m/z): 207 [M+H]; A solution of 2,3-dihydro-1H-indole-2,3-dione (1 eq.) and sodium hydroxide (1.1 eq.) in water was stirred for 5-30 mm at 25 C. Then a solution of sodium nitrite (1 1 eq.) in water and concentrated sulfuric acid (2 eq.) were added dropwise with stirring at 0.-10 C. After 5-30 mm a solution of SnC12 (2.5 eq.) in concentrated hydrochloric acid (15-30 eq.) was added slowly. After5 being stirred for 1–5 h at 25 C the reaction mixture was filtered and the solid was dissolved in methanol. Sulfuric acid (0.5-1 eq.) was added to the solution and the solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum to give the ester which may need further purification such as fresh chromatography.

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 774-47-0, The chemical industry reduces the impact on the environment during synthesis 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: In an ordinary vial equipped with a Teflon-coated stir bar, thiourea IV or V (0.04 mmol, 11.89 mg, 20 mol %) was dissolved in 1.0 mL of THF. Then the corresponding isatins 1 (0.1 mmol, 1.0 equiv) was added, followed by the addition of alpha,beta-unsaturated ketones 2 (0.2 mmol, 2.0 equiv). The vial was capped with a rubber stopper and the mixture was stirred at room temperature for the time given in the tables. The crude mixture was then purified by flash column chromatography silica gel, using hexane/ethylacetate 2:1 as the eluent. Solvent was removed in vacuo to give the desired products.

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, 5,6-Difluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Guo-Gui; Zhao, Hua; Lan, Yu-Bao; Wu, Bin; Huang, Xiao-Fei; Chen, Jian; Tao, Jing-Chao; Wang, Xing-Wang; Tetrahedron; vol. 68; 20; (2012); p. 3843 – 3850;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

7-Fluoroisatin (1 mmol) was added to the microwave reaction tube,4-hydroxycoumarin (1.1 mmol),Tetrabutylammonium chloride (0.1 mmol) and water (4 mL),Microwave power 400W,60 radiation 15min,Stop microwave radiation,Cool to room temperature,Vacuum suction filtration,The filter cake was washed with ice-ethanol (0.5 ml)Drying under reduced pressure,A white solid,Yield 94%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroisatin, its application will become more common.

Reference:
Patent; Zunyi Medical College; Zhang Lei; Wang Jing; Liu Lai; Zheng Chengyue; Wang Yang; (4 pag.)CN107098888; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem