Category: indolines-derivatives

Synthetic Route of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The general synthetic approach involved condensation of an equimolar mixture of corresponding substituted indole-2,3-dione (0.01 mol) and substituted pyrazole (0.01 mol) in absolute ethanol in the presence of 2,3-drops of glacial acetic acid for 3-4 h. On cooling, flakes separated out which were filtered and recrystallized from hot ethanol to give shining bright needles of Schiff base.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chinchole; Wankhede; Asian Journal of Chemistry; vol. 30; 10; (2018); p. 2220 – 2224;,
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Reference of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The chemical industry reduces the impact on the environment during synthesis 1-Acetylindolin-3-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, 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. Recommanded Product: 7-Bromo-2,3-dihydro-isoindol-1-one

[00309] To a solution of 7-bromoisoindolin-l-one 1 (212 mg, 1.0 mmol) in MeCN (5.0 mL) was added CS2CO3 (652 mg, 2.0 mmol). The reaction mixture was stirred at rt for 15 min then cooled to 0-5 C. Benzyl bromide (274 mg, 1.6 mmol) was added dropwise. The reaction mixture was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between EtOAc and water and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20% EtOAc in hexanes) to afford compound 2 (220 mg, 73%) as a yellow solid. 1H MR (400 MHz, CD3OD): delta 7.68 (m, 1H), 7.46 – 7.54 (m, 2H), 7.32 – 7.41 (m, 5H), 4.83 (s, 2H), 4.37 (s, 2H).

The synthetic route of 200049-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
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Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, molecular formula is C8H4ClNO2, 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 7-Chloroisatin

In a 100 mL round bottom flask, according to the feed ratio (7-chloroisatin: ethanol (1:1.5); 7-chloroisatin: 1-phenylmalonaldehyde (1:1.2))Add 7-chloroisatin 80 mg (0.44 mmol), ethanol 30.4 mg (0.66 mmol) and 1-phenylmalonaldehyde 78.4 mg (0.53 mmol), respectively.Adding a catalytic amount (0.1 times equivalent of 7-chloroisatin or its derivative) of 007×7, ferrocene and palladium acetate, 25 mL of solvent tetrahydrofuran, heating to 80 ° C, and heating for 6 hours.The reaction was monitored by thin layer chromatography. After the reaction was completed, the heating was stopped, the condensing device was removed, the mixed system was concentrated under reduced pressure, and purified by column chromatography.The title compound (12) was obtained by drying to give 120.8 mg,yield of 81percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7477-63-6, its application will become more common.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Ding Shunjun; Wang Xuechuan; Dong Hao; Wang Qiang; (15 pag.)CN108395438; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, SDS of cas: 7477-63-6

General procedure: To the respective solution of isatins 1a-g (1 mmol) inDMF(3mL) were added K2CO3 (165.5mg, 1.2 mmol). The resultingmixtures were stirred at 80 C for 1 h, then KI (8.3 mg,0.05 mmol) was added. After stirring for further 15 min,0.15mL of a solution of propargyl bromide 80% in toluenewas added dropwise slowly into the mixtures. The reactionmixtures were again stirred at 60 C for 3 h. Upon completionof the reaction, the resulting mixtures were cooled, pouredinto ice-cold water and acidified to pH?4. The orange solidsformed were filtered and dried to give the propargylatedisatins2, which were used for the next step without furtherpurification.

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dung, Do Thi Mai; Hai, Pham-The; Anh, Duong Tien; Huong, Le-Thi-Thu; Yen, Nguyen Thi Kim; Han, Byung Woo; Park, Eun Jae; Choi, Yeo Jin; Kang, Jong Soon; Hue, Van-Thi-My; Han, Sang-Bae; Nam, Nguyen-Hai; Journal of Chemical Sciences; vol. 130; 6; (2018);,
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Electric Literature of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 5-bromo-1,3-dihydro-2H-indole-2-one (1.272 g, 6 mmol) in THF(15 ml) was added a solution of NaN(SiMe3)2 in THF (30 ml, 30 mmol). The reaction mixture was cooled to -78 C and stirring was continued at the same temperature for 0.5 h. The 2-chloro-N-(2-chloroethyl)-N-methyl ethylamine hydrochloride (1.155 g, 6 mmol) was added to the mixture, continued to stir at -78 C for 0.5 h, then stirred for 2 d at room temperature (TLC control). 4 M HCl (10 ml) was added, the mixture was adjusted pH to 10 with concentrated ammonia and extracted with CH2Cl2 (3 × 20 ml). The combined organic layer was dried (3 g of Na2SO4) and concentrated to afford the crude product, which was purified by FC with MeOH/CH2Cl2.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ye, Lianbao; Tian, Yuanxin; Li, Zhonghuang; Jin, Hong; Zhu, Zhengguang; Wan, Shanhe; Zhang, Junyan; Yu, Pengjiu; Zhang, Jiajie; Wu, Shuguang; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 370 – 375;,
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Application of 4403-36-5, 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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound has unique chemical properties. The synthetic route is as follows.

(2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamide To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl amine (0.060 g, 0.143 mmol) in methylene chloride (3 mL) was added 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride (0.043 g, 0.150 mmol) and triethylamine (0.060 mL, 0.43 mmol) and the solution was stirred 1 hr at ambient temperature. The reaction was diluted with saturated aqueous sodium hydrogen carbonate and extracted with methylene chloride. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.073 g, 77%).

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

Reference:
Patent; Blumberg, Laura C.; Brown, Matthew F.; Gladue, Ronald P.; McGlynn, Molly A.; Poss, Christopher S.; US2002/107255; (2002); A1;,
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Synthetic Route of 3484-35-3, 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. 3484-35-3 name is 5-Methylindolin-2-one, 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.

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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
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These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. category: indolines-derivatives

General procedure: A reaction flask with high vacuum valve was charged with 2-amino-N?-arylbenzohydrazides (1.0 mmol), 4-halogenated isatins (1.0 mmol), CuI (10 mg, 0.05 mmol), and Cs2CO3 (650 mg, 2.0 mmol). After being degassed by three freeze-thaw pump cycles, THF (10.0 mL) was injected into the mixture. And then, the reaction mixture was stirred at reflux for 10?16 h before reaching completion, which was monitored by TLC. The solvent was recovered by distillation under reduced pressure, and the residue was purified by chromatography over silica gel to give 3 using ethyl acetate and petroleum ether (1:2) as an eluent.

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

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
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These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
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