Author: Jessica.F

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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

General procedure: A mixture of isatin (1 mmol), malononitrile or cyanoacetic esters (1 mmol), 1,3-dicarbonyl compounds (1 mmol), and the catalyst (10 wt %) in ethanol (3 ml) was stirred at 80 C for a specified time (see Table 2). After complete conversion, as indicated by TLC, the reaction mixture was cooled to room temperature. The resulting solid precipitate was filtered and dried along with the catalyst. Further purification of the product was performed by recrystallization using ethanol and the catalyst was recovered by filtration.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 611-09-6.

Reference:
Article; Maheshwar Rao; Reddy, G. Niranjan; Reddy, T. Vijaikumar; Devi, B.L.A. Prabhavathi; Prasad; Yadav; Reddy, B.V. Subba; Tetrahedron Letters; vol. 54; 20; (2013); p. 2466 – 2471;,
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Reference of 774-47-0, 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 774-47-0 as follows.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

According to the analysis of related databases, 774-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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Electric Literature of 7699-18-5, 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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-methoxy-2,3-dihydro-1H-indole-2-one (5 g, 30.64 mmol) and diisopropylamine (6.14 g, 60.79 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added n-butyllithium (49 mL, 122.68 mmol, 2.5 M n-hexane solution).The mixture was stirred for 1 hour and 1,2-dibromoethane (6.89 g, 36.68 mmol) was slowly added.The mixed solution was transferred to room temperature for reaction. The reaction was then quenched by adding 100 mL of water,And extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over anhydrous sodium sulfate,Suction filtered and concentrated in vacuo. Passing a gradient flash column (ethyl acetate / petroleum ether) gave compound 10 as an off-white solid, 2.5 g, yield 43%.

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

Reference:
Patent; Guangdong Pharmaceutical University; Ye Lianbao; Shi Peiqi; Zhu Daqian; Zhao Tao; Chen Weiqiang; Gao Wei; Luo Yan; (27 pag.)CN110256429; (2019); A;,
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Synthetic Route of 675109-45-2,Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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.

3H:; [00255] Intermediate 2 (164 mg, 1.11 mmol), 3G (535 mg, 1.00 mmol), and glyoxylic acid monohydrate (111 mg, 1.21 mmol) were taken up in CH3CN (3 mL) and DMF (2 ml). The mixture was stirred at 600C for 48 h, then was concentrated. The crude product was purified by flash chromatography (1 to 20% MeOH/CH2Cl2 gradient) to afford 313 mg of 3H as a pale yellow solid. MS (ESI) m/z 693.3 (M+H)+

The synthetic route of 675109-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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: 24566-79-8

Triphenylmethanethiol (11.90 g, 43.08 mmol) was suspended in DMSO (40 mL). DBU (7.41 mL, 49.55 mmol) and 6-bromohexylphthalimide (13.32 g, 42.94 mmol) were added, and the mixture was allowed to react for approximately 15 min. The reaction mixture was partitioned between ethyl acetate (700 mL) and 0.1 M HCl (200 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL), and the combined organic fractions were washed with NaHCO3 sat. (80 mL) and brine (80 mL), dried over MgSO4, filtered and concentrated. The crude yellow oil was recrystallized from n-heptane/ethyl acetate. The intermediate 6-(S-Trityl-)mercaptohexylphthalimide was obtained as a white solid (13.3 g, 26.4 mmol, 62%).

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; Sprogoe, Kennett; Cleemann, Felix; Hersel, Ulrich; Kaden-Vagt, Silvia; Lessmann, Torben; Rau, Harald; Wegge, Thomas; (61 pag.)US9265723; (2016); B2;,
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Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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.

Example 8 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (82 mg, 0.2 mmol), 2-oxoindoline-6-carboxylic acid (36 mg, 0.2 mmol), EDCI (76 mg, 0.4 mmol) and N-methylimidazole (50 mg, 0.6 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by preparative TLC (Silica gel, 20 cm*20 cm, separated by EtOAc, eluted by DCM_MeOH=1:20, v/v) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide (25 mg, 23.5%). 1H NMR (300 MHz, DMSO): delta 10.52 (s, 1H), 9.56 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 7.90 (brs, 1H), 7.48-7.46 (m, 2H), 7.28-7.25 (m, 2H), 6.93-6.90 (m, 1H), 4.54 (brs, 1H), 3.77-3.34 (m, 11H), 2.50-2.34 (m, 1H), 2.07-1.99 (m, 2H). LC-MS: 532 [M+H]+, 530 [M-H]-, tR=1.35 min. HPLC: 97.39% at 214 nm, 97.05% at 254 nm, tR=4.54 min.

Statistics shows that 2-Oxoindoline-6-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 334952-09-9.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
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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 61-70-1 as follows. Application In Synthesis of 1-Methylindolin-2-one

To 10 ml schlenk bottle adding N – methyl -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N – methyl -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N – methyl isatin, I – 2, the isolation yield is 73%,1

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4N2O4

General procedure: A mixture of isatins or acenaphthoquinone (1 mmol), activated methylene reagents (1 mmol), 1,3-dicarbonyl compounds (1 mmol) and SBA-15-DABCO (0.085 g, 7 mol%) in water was stirred at 25 or 50 C. Upon compilation, monitored by TLC (n-hexane / ethyl acetate 2 / 1), the reaction mixture was allowed to cool to room temperature. The precipitate was filtered and dissolved in acetone. The catalyst was separated by filtration of this solution. The solution was concentrated under vaccum to afford the product, which was purified by recrystallization in the ethanol.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baharfar, Robabeh; Azimi, Razieh; Synthetic Communications; vol. 44; 1; (2014); p. 89 – 100;,
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Synthetic Route of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

A 25 mL flask was charged with 2-amino-5-methyl-N?-phenylbenzohydrazide (241 mg, 1.0 mmol), 4-bromoisatins (226 mg, 1.0 mmol), CuI (10mg, 0.05 mmol), and THF (10.0 mL). The reaction mixture was stirred at reflux for 4 h before reaching completion, which was monitored by TLC. The insoluble was filtered off by a fast hot-filtration, and the product 4a was obtained directly via filtration when the mixture was allowed to cool down to the room temperature. 4.2.1. 4-Bromo-6′-methyl-3′-(phenylamino)-1’H-spiro[indoline-3,2′-quinazoline]-2,4′(3’H)-dione (4a). Yield 92percent (448 mg). Pale yellow solid, mp: 186-187 °C; 1H NMR (DMSO-d6, 400 MHz): deltaH 2.19 (s, 3H), 6.54 (d, J=8.0 Hz, 1H), 6.67 (s, 1H), 6.78-6.87 (m, 3H), 7.01 (s, 2H), 7.10-7.19 (m, 3H), 7.39 (s, 1H), 7.53 (s, 1H), 7.79 (s, 1H), 10.61 (s, 1H). 13C NMR (Acetone-d6, 100 MHz): deltaC 19.9, 80.3, 109.48, 109.54, 112.5, 113.4, 114.6, 120.2, 126.3, 126.5, 127.4, 128.1, 132.0, 132.1, 134.9, 143.87, 143.94, 148.1, 170.1, 173.8. IR (KBr): nu 3436, 3331, 3298, 1728, 1621, 1518, 1446, 1416, 1356, 1306, 1242, 1214, 1174, 1158, 1078, 1044, 989, 967, 942, 903, 777, 750, 731 cm-1. HRMS (TOF, ESI, m/z): Calcd for C22H16BrN4O2 [M-H]- 447.0457, found 447.0483.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisatin. I believe this compound will play a more active role in future production and life.

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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Adding a certain compound to certain chemical reactions, such as: 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, 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 897957-06-1, HPLC of Formula: C9H8BrNO

General procedure: Under N2, sodium ( 0.5 g ) was reacted with 30 ml ethanol. When the solution was clear,2.9 g N-Me oxindole was added followed by 3.1 g diethyl carbonate and the resulting reactionmixture was refluxed for 15 hours. Then cooled to room temperature and added to 3Nhydrochloric acid solution ( pH = 2 ). The resulting solution was extracted with ether for threeEntry Catalyst time (h) yieldb(%) drc eed(%)1 3e 5 96 72:28 38e/382 3f 8 96 74:26 21e/33 3g 2 99 73:27 11e/334 3h 8 96 71:29 6e/335 3i 2 95 59:41 1e/26 3j 10 94 68:31 44/1e7 3k 2 93 67:33 1/18 3l 72 61 69:31 8/1times. The organic extracts were combined and dried over magnesium sulfate. Thenconcentrated in vacuo and washed with petroleum ether to give 2.7 g2-oxindole-3-carboxylates 1a (61%) as light 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, 6-Bromo-1-methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Jing; Jia, Li-Na; Peng, Lin; Wang, Qi-Lin; Tian, Fang; Xu, Xiao-Ying; Wang, Li-Xin; Tetrahedron; vol. 70; 21; (2014); p. 3478 – 3484;,
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