Category: indolines-derivatives

Electric Literature of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-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.

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 ML of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide.. The mixture was stirred for 1 hour, diluted with 100 ML 50% acetic acid in water and filtered.. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off-white solid.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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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. 87-48-9, name is 5-Bromoindoline-2,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: The suspension of isatin 1a-c in hydrazine hydrate was refluxed for 5h until clear solution formation. After reaction completion the mixture was cooled down to room temperature and poured into cold water. Then pH value of the mixture was adjusted to 1-2 via concentrated hydrochloride acid addition. The reaction mixture was left at room temperature for 2-3days, the precipitate formed was filtered, washed with water and dried on air and was used without additional purification. The following compounds were obtained according to this general procedure:

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; Lozinskaya, Natalia A.; Babkov, Denis A.; Zaryanova, Ekaterina V.; Bezsonova, Elena N.; Efremov, Alexander M.; Tsymlyakov, Michael D.; Anikina, Lada V.; Zakharyascheva, Olga Yu.; Borisov, Alexander V.; Perfilova, Valentina N.; Tyurenkov, Ivan N.; Proskurnina, Marina V.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry; vol. 27; 9; (2019); p. 1804 – 1817;,
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Synthetic Route of 3335-98-6, 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 3335-98-6 as follows.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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These common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, 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. Safety of 3,3-Dimethylindoline

EXAMPLE 1 STR12 In 0.7 ml of thionyl chloride, 0.13 g of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid hydrochloride (containing sodium chloride) was refluxed for 30 minutes, and volatile components were removed by distillation under reduced pressure. The residue was added to a solution of 0.15 g of 3,3-dimethylindoline and 0.15 ml of triethylamine in 2 ml of dichloromethane under ice-cooling. After stirring the mixture at room temperature overnight, 5 ml of a sodium carbonate aqueous solution was added thereto, and the mixture was extracted with chloroform. The organic layer was dried, and the solvent was removed by distillation under reduced pressure. The residue was subjected to silica gel column chromatography using chloroform/methanol as an eluent to obtain 0.11 g of 5-[(2,3-dihydro-3,3-dimethylindol-1-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole as an oily substance.

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

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5344927; (1994); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Oxoindoline-5-carboxylic Acid

264 mg (1.1 mmol) of (S)-2-cyclopropylaminomethyl-pyrrolidine-1-tert-butyl carboxylate is added to a solution of 177 mg (1 mmol) of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (prepared according to the following procedure: Li Sun, Ngoc Tran, Congxin Liang, Flora Tang, Audie Rice, Randall Schreck, Kara Waltz, Laura K. Shawver, Gerald McMahon, and Cho Tang, Journal of Medicinal Chemistry, 1999, Vol. 42, 25, 5120), 417 mg (1.1 mmol) of O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium, 646 mg (5 mmol) of diisopropylethylamine and 27 mg (0.1 mmol) of 1-hydroxybenzotriazole in 2 ml of dimethylformamide, then the reaction mixture is stirred at room temperature for 30 minutes. The solvent is evaporated, then the product is extracted with ethyl acetate. The organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on silica (ethyl acetate/methanol 95/5 then 9/1) to give 254 mg (64%) of (S)-2-{[cyclopropyl-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-amino]-methyl}-pyrrolidine-1-tert-butyl carboxylate in the form of a beige solid.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pierre Fabre Medicament; US2009/42876; (2009); A1;,
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Synthetic Route of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of Ca(OH)2 (38.5 g, 519 mmol) and 5-(trifluoromethoxy)isatin (40 g, 173 mmol) in water (150 ml) was heated at 80C for 1 h. The heating bath was removed followed by slow addition of chloroacetone (34.5 ml, 433 mmol). The reaction was then heated at 80C for another 5 h then cooled to RT and quenched with IN aq. HCl until pH=2. The solid was filtered over fritted disk, washed with water and dried overnight at 50C under high vacuum to afford the product intermediate (47.0 g, 95% yield) as a slightly yellow solid.

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-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; BARA, Thomas; BHAT, Sathesh; BISWAS, Dipshika; BROCKUNIER, Linda; BURNETTE, Duane; CHACKALAMANNIL, Samuel; CHELIAH, Mariappan, V.; CHEN, Austin; CLASBY, Martin; COLANDREA, Vince, J.; GUO, Zhuyan; HAN, Yongxin; JAYNE, Charles; JOSIEN, Hubert; MARCANTONIO, Karen; MIAO, Shouwu; NEELAMKAVIL, Santhosh; PINTO, Patrick; RAJAGOPALAN, Murali; SHAH, Unmesh; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; XIA, Yan; WO2014/25736; (2014); A1;,
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Related Products of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

Weigh 6-chloroguanidine 0.3g (0.0017mol),5-chloroindole anhydride0.36 g (0.0018 mol) was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.It was dried, weighed 0.34 g, and the yield was 63.0%.

The chemical industry reduces the impact on the environment during synthesis 6-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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Synthetic Route of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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 solution of 6-bromo-2-methylisoindolin-1-one (5 g,22.1 mmol) in dmf (30 mL) was added bis(pinacolato)diboron (6.18 g,24.3 mmol) and potassium acetate (6.51 g,66.4 mmol). The reaction mixture was degassed and backfilled with N2 gas,and 1,1 ?-bis(diphenylphosphino)fenocene palladium(II)dichloride dichloromethane (0.903 g,1.106 mmol) was added.The reaction mixture was stined at 80 C for 10 hours. After diluting with EtOAc and water, The organic layer was concentrated and purified on silica column (100% EtOAc) to get the product as a mixture of the title compound as a boronic ester and boronic acid,which was not further purified.MS: 274 (m+1)?H NMR (500 MHz,CDCl3): oe 8.33 (s,1H),7.98 (d,7.5 Hz,1H),7.46 (d,7.5 Hz,1H),4.41 (s,2H),3.22 (s,3H),1.38 (s,12H). The following intermediates in table c were preparedaccording to scheme c using the procedure outlined in the synthesis intermediate cl using 1,1?-bis(di-tert-butylphosphino)fenocene palladium dichloride or 1,1 ?-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane complex as the palladium catalyst with toluene or dmf as the reaction solvent. The starting material bromide was either commercially available,known in the literature,or prepared using the protocol in scheme B.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John J.; BAO, Jianming; EGBERTSON, Melissa; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra Lee; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert D., Jr.; MENG, Zhaoyang; RUDD, Michael T.; SELYUTIN, Oleg; TELLERS, David M.; TONG, Ling; WAI, Jenny Miu-Chun; (125 pag.)WO2017/107089; (2017); A1;,
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Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. Product Details of 552330-86-6

Toa solution of6F (6 g, 28 mmol)in MeOH(IOO mL), palladium acetate (0.12g), Et3N (8.6 g, 85 mmol) and Xantphos (0.6g) were added. The reactionmixturewas stirredat 140 C under CO (3 MPa)overnight.Themixturewas cooled to room temperature and filtered.The filtrate was concentrated in vacuum to provide 6G (6 g). 1H-NMR (400 MHz, DMSO_d6): 8.82-8.84 (s,IH),8.16-8.18 (s,IH), 8.05-8.07(s, IH), 7.79-7.8l(s,IH), 4.44-4.46 (s, 2H), 3.90-3.92 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.

Reference:
Patent; BAIKANG (SUZHOU) CO., LTD; HAN, Jie; WO2015/81891; (2015); 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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

In a 100 mL single-mouth bottle, dihydroindole-5-carboxylic acid methyl ester (800 mg, 4.50 mmol) was added and methanol was added.(15 mL) was dissolved, followed by the addition of potassium hydroxide (760 mg, 13.5 mmol), and reacted at 45 C for 15 h. After the reaction was completed,Dilute with 100 mL of water, then adjust the pH to 2 with 2M diluted hydrochloric acid, and use dichloromethane (50 mL×3).Drying and spinning off the solvent gave the title compound.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Ge Chongxun; Huang Yiqiang; Cao Chen; Li Qingqing; Hou Shaohua; (63 pag.)CN108276382; (2018); A;,
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