Tag: M.W=200-300

2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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: 2436-29-5

Bromine (0.22 ml, 4.29 mmol) was added dropwise to a solution (30 ml) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal (866 mg, 4.36 mmol) in acetic acid at room temperature. After stirring at room temperature for 2 hours, the reaction solution changed in color from brown to colorless. Thiourea (373 mg, 4.90 mmol) was added to the reaction solution and the resulting mixture was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with methanol-diethyl ether and then dried. The solvent was distilled off under reduced pressure to obtain the title compound (616 mg, 55.8%).; LC/MS (M+1, retention time): 260.0, 3.76 min.

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1640369; (2006); A1;,
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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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6-Bromo-7-fluoroindoline-2,3-dione

To a mixture of 6-bromo-7-fluoroindoline-2,3-dione (18.9 g, 77.5 mmol) in 2 N NaOH (350 mL) at 0 oC, H2O2 (30%, 40 mL) was added. The mixture was stirred at room temperature for 16 h. The mixture was quenched with Na2SO3, and the mixture was acidified with conc. HCl to adjust pH to 2. The precipitate was collected by filtration and dried to afford the desired product as a white solid (17 g, 94% yield).

According to the analysis of related databases, 1336963-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (335 pag.)WO2016/164675; (2016); A1;,
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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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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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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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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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Related Products of 87-48-9, 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. 87-48-9 name is 5-Bromoindoline-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.

5-bromo-indole-2,3-dione (2.25g, 10mmol), ethylene glycol (45 mL) and heatIt was added KOH (1.68g, 30mmol) in a mixture of hydrazine hydrate (1.06g, 21.10mmol). The reaction mixture was stirred for 4 hours at 80 C.. The mixture was cooled to room temperature, poured into ice-cold water, with 12N hydrochloric acid was adjusted to pH 1 ~ 2, and stirred at room temperature for 12 hours. The mixture was filtered solid was washed with water (5 mL), and dried to give the crude product which was purified juice dim over a column chromatography (methanol in dichloromethane, 0.5% v / v), 0601 -194 as a yellow solid (785mg, 37%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
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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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., SDS of cas: 118289-55-7

Examples 1. Preparation of ZPR in n-BuOH with 0.9 mol NaI. In a three necked flask was charged n-BuOH (50 ml) and 1, 2-Benzisothiazole-3- piperazinyl hydrochloride (BITP HC1) (5.6g, 0.022 mol), and the obtained slurry was heated at 100C. To the slurry, Na2CO3 (11.6 g), NaI (3g) and 5- (2-chloroethyl)-6- chloro-1, 3-dihydro-indole-2 (2H)-one (CEI) (7. 5g, 0.032 mol) were added at 110C. The heating was maintained for 8. 5h. After cooling the reaction product was filtrated, washed with hexane and water, and dried at 60 C. The dried product weights 8.12g and has an HPLC purity 92.7%.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
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