Indolines-derivatives

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. 1504-06-9, name is 3-Methyloxindole, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Methyloxindole

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

[0521] The 5-CHLORO-7-METHYL-LH-INDOLE-2, 3-dione (25.0 g, 0.13 mol), potassium hydroxide (8.4 g, 0.15 mmol) and 30% hydrogen peroxide (21.6 g, 0.18 mol) were mixed together in methanol (300 mL) at 0C for 2 h followed by 16 h at room temperature. The solution was poured into ethyl acetate (500 mL) and extracted with 1 N hydrochloric acid (3 x 200 mL) followed by brine (1 x 50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The 2-amino-5-chloro-3-methylbenzoic acid (18.0 g, 0.10 mmol) was isolated as a yellow solid (75% yield). HRMS 7NEZ 185.0238 ; calcd 185.0244.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

Commercially available 4-aminophthalimide (500 mg, 3.08 mmol) was dissolved in acetonitrile (15 mL). To the mixture were added cesium iodide (961 mg, 3.70 mmol), iodine (947 mg, 3.70 mmol), and copper iodide (712 mg, 3.70 mmol) at room temperature, and then an 11% aqueous hydrogen iodide solution (15 mL) and isoamyl nitrite (1.24 mL, 9.24 mmol) at 0C. The mixture was stirred at room temperature for 6.5 hours, and then for 1.5 hours after adding isoamyl nitrite (4.96 mL, 37.0 mmol). Then, saturated sodium bicarbonate was added to the mixture, and after filtration through sellite, the organic layer was separated. The resulting organic layer was washed with a saturated aqueous sodium thiosulfate solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was triturated with chloroform, and the resulting solid was filtered off and dried to give 4-iodophthalimido (394 mg, 47%). ESI-MS: m/z 272 [M-H]-.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
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Electric Literature of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-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.

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
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Electric Literature of 4403-36-5, The chemical industry reduces the impact on the environment during synthesis 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, I believe this compound will play a more active role in future production and life.

To 3-exo-[(S)-1-((S)-2-methyl-propane-2-sulfinylamino)-2-(2,4,5-trifluoro-phenyl)-ethyl]-8-aza- bicyclo[3.2.1]octane (540 mg, 1.2 mmol) in dichloromethane/1 M NaOH (1/1, 5 mL) is added 2-phthalimidoethane sulfonyl chloride (1.101 g, 3.59 mmol) then the resulting mixture is stirred at 500C during 16h. It is extracted with dichloromethane, the organic phase is dried and evaporated to give a white solid. MS: 626 [M+H]+HPLC (Zorbax SB C18, 2min method (0-0.8min 10-95%ACN, 0.8-1.5min 95%ACN, 1.5- 1.6min 95-10%ACN, 1.6-2min 10%ACN): 1.44 min.

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-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/115821; (2007); A2;,
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Some common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, 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. Product Details of 324-03-8

General procedure: Target compounds 3 were prepared by coupling compounds 1 or 2 with hydrazine hydrate under a mild condition. A mixture of isatin or an N1-substituted isatin (10 mmol) and hydrazine hydrate (5 mmol) was refluxed in ethanol (50 mL) in the presence of acetic acid as the catalyst for 0.5-2 h. After completion of the reaction (monitored by TLC), the solvent was removed under reduced pressure and the crude product was washed with water and recrystallized from ethanol to give pure products (Table 1). Some compounds synthesized in the current study are known compounds and their physicochemical characteristics are consistent with those reported in earlier literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 324-03-8, its application will become more common.

Reference:
Article; Liang, Chengyuan; Xia, Juan; Lei, Dong; Li, Xiang; Yao, Qizheng; Gao, Jing; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 742 – 750;,
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These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. Computed Properties of C8H4ClNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 °C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
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Electric Literature of 90725-50-1, 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. 90725-50-1, name is 6-Bromo-3-methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The compound [78-1] obtained in the process (1) (4.9 g) was suspended in toluene (22 mL), and borane dimethyl sulfide complex (4.4 mL) was added at 0C, and then the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled with ice-water bath, and an aqueous solution of 5N-sodium hydroxide (8 mL), an aqueous solution of 8N-sodium hydroxide (8 mL) and ethyl acetate (8 mL) were added, successively, and then the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL), and triethylamine (4.55 mL) and a solution of di-tert-butyl dicarbonate (6.2 g) in tetrahydrofuran (10 mL) were added successively at room temperature, and then a grain of dimethylaminopyridine was added, and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (4.6 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 8. 03 (1H, s), 7. 07 (1H, dd, J = 7.9, 1.6 Hz), 6.96 (1H, d, J = 8.3Hz), 4.19-4.08 (1H, m), 3.57-3.43 (1H, m), 3.39-3.27 (1H, m), 1.53 (9H, brs), 1.30 (3H, d, J = 6.8 Hz). ESI-MS found: 256 [M-tBu+H]+

The synthetic route of 6-Bromo-3-methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
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Reference of 32692-19-6, 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 32692-19-6 as follows.

To a solution of 5-nitroindoline (5.718 g) in DMF (60 mL) at 0C was sequentially added Nai l (1.348 g, 60% dispersion in mineral oil) and l-bromo-2-methoxyethane (5.368 g). The mixture was stirred at 0C for 2 h, and then was allowed to warm up to room temperature and stirred for another 3 h. At this point, TLC indicated the reaction to be complete. The reaction mixture was poured onto ice-water. The precipitate was collected, and re-dissolved in ethyl acetate. The organic layer was washed with water, brine and concentrated under reduced pressure to afford the desired product 1 (7.292 g, 94%, M+H+= 223.3) as a yellow solid.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
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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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., COA of Formula: C9H7NO3

2-Oxo-3-(4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrol-1-ylmethylene)-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-5-carboxylic acid was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 325.2 [M++1].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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