Category: 20780-72-7

In chemical reaction engineering, simulations are useful for investigating and optimizing a particular reaction process or system., name: 4-Bromoisatin

9-Bromo-5H-[1,2,4]triazino[5,6-b]indole-3-thiol 5-Bromoisatin (1.0 g, 4.45 mmol), thiosemicarbizide (405 mg, 4.45 mg) and K2CO3 (920 mg, 6.67 mmol) were suspended in water (50 mL). The reaction mixture was stirred at reflux for 16 h over which time the dark brown suspension became a clear light brown solution. The solution was carefully acidified by dropwise addition of AcOH and resulting precipitate was filtered. The precipitate was recrystallised from DMF to yield a red solid (1.18 g, 95percent). deltaH (500 MHz, DMSO-d6, 363K) 7.43-7.52 (3H, m), 14.68 (1H, br s) deltaC (125 MHz, DMSO-d6) 113.0, 117.0, 118.3, 127.4, 133.5, 136.1, 145.3, 149.9, 180.0 mp>300° C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20780-72-7, its application will become more common.

Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); 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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., Reference of 20780-72-7

General Procedure 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. 4-(o-Tolyl)indoline-2,3-dione Following General Procedure 3,4-bromoisatin (100 mg, 0.44 mmol), potassium 2-methyphenyltrifluoroborate (123 mg, 0.62 mmol), K3PO4 (338 mg, 1.59 mmol) and Pd(PPh3)2Cl2 (31 mg, 0.04 mmol) in THF/H2O (3:1, 3 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid (65 mg, 59percent). deltaH (500 MHz, DMSO-d6) 2.15 (3H, s), 6.93 (2H, m), 7.14 (1H, d, J=7.6 Hz), 7.20-7.26 (1H, m), 7.30 (1H, d, J=7.3 Hz), 7.32-7.37 (1H, m), 7.56 (1H, app t, J=7.9 Hz), 8.84 (1H, br s) deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0 mp 161-162° C.

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Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); A1;,
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Related Products of 20780-72-7, 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 20780-72-7 as follows.

General procedure: Isatin 1 (147.1 mg, 1 mmol), (E)-1-phenylpent-2-ene-1,4-dione (2a, 348.4 mg, 2 mmol), and thiourea I (57 mg, 0.1 mmol) were cooled to -20 °C, dissolved in toluene (3 mL), and the mixture was stirred at -20 °C for 24 h. The progress of the reaction was monitored by TLC and NMR spectroscopy. The product was isolated by direct column chromatography on silica gel (CH2Cl2/EtOAc 95:5 to 85:15)

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; Trubitson, Dmitri; ?ari, Sergei; Kaabel, Sandra; Kudrjashova, Marina; Kriis, Kadri; Jaerving, Ivar; Pehk, Tonis; Kanger, Tonis; Synthesis; vol. 50; 2; (2018); p. 314 – 322;,
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Indoline | C8H9N – PubChem

Formula: C8H4BrNO2, Having gained chemical understanding at molecular level, chemistry graduates may choose to apply this knowledge in almost unlimited ways, as it can be used to analyze all matter and therefore our entire environment.

Take 4-bromoindole dione 2.0g (8.85mmol) into a 25mL round bottom flask, add 5mL N, N-dimethylformamide, was added with stirringK2CO3 3.66g (26.5mmol), and finally added methyl iodide (10.6mmol) at room temperature for 4h.After completion of the TLC detection reaction, 15 mL of water was added to the reaction solution, which was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate,Using developing solvent petroleum ether: ethyl acetate = 5: 1,200-300 mesh silica gel column chromatography to give 2.8 g of 1-methyl-4-bromoindodione, yield 67percent.

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Reference:
Patent; Tianjin University of Science and Technology; Yu Peng; Sun Hua; Han Kailin; Li Yashan; Peng Xiaolin; Teng Yuou; Zhang Yazhou; (26 pag.)CN104725372; (2017); B;,
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Career opportunities within science and technology are seeing unprecedented growth across the world, and those who study chemistry or another natural science at university now have increasingly better career prospects. category: indolines-derivatives

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 percent) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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name: 4-Bromoisatin, Chemistry built the modern world, from the materials that make up the everyday objects around us, the batteries in our devices and cleaning products that help to maintain sanitation.

To a solution of 4-bromoisatin 30 (100 mg, 0.44 mmol) in degassed THF/H2O (3:1, 3 mL) was added potassium 4-methyphenyltrifluoroborate (123 mg, 0.62 mmol) and K3PO4 (338 mg, 1.59 mmol) followed by Pd(PPh3)2Cl2 (31 mg, 0.04 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 °C. The reaction mixture was cooled to rt, diluted with EtOAc (5 mL) and filtered through Celite®. The organic solution was washed with brine (5 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 30-40 °C petrol/acetone, 4:1) to afford the title compound (42) as an orange solid (72 mg, 68percent); mp 178-179 °C; numax (solid) 3274, 3051, 2906, 1741, 1609, 1486; deltaH (400 MHz, CDCl3) 2.43 (3H, s, CH3), 6.88 (1H, d, J = 8.0 Hz, C(7)H), 7.08 (1H, d, J = 8.0 Hz, C(5)H), 7.28 (2H, d, J = 8.5 Hz, C(3′)H and C(5′)H), 7.45 (2H, d, J = 8.5 Hz, C(6′)H and C(2′)H), 7.55 (1H, app t, J = 8.0 Hz, C(6)H), 8.70 (1H, br s, NH); deltaC (125 MHz, CDCl3) 21.4, 110.8, 114.4, 125.9, 128.8, 129.0, 133.1, 138.0, 139.4, 143.8, 154.2, 159.2, 178.3; m/z (ESI-) 236 ([M-H]-, 100percent); HRMS (ESI-) C15H10NO2S- ([M-H]-) requires 236.0717; found 236.0716.

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Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
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20780-72-7, name is 4-Bromoisatin, 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. Quality Control of 4-Bromoisatin

General procedure: To a stirred solution of N-Boc-3-pyrrolin-2-one (1, 36.6 mg, 0.20 mmol), K2CO3 (2.8 mg, 0.020 mmol,20 mol percent) in water (2.0 mL), was added isatin (2a, 14.7 mg, 0.10 mmol) at room temperature. Thereaction mixture was stirred for 4 h (monitored by TLC). The reaction mixture was then extracted withethyl acetate (3 x 5 mL). The combined organic layers were dried with Na2SO4 and the solvent wasthen evaporated under reduced pressure. The crude reaction mixture thus obtained was purified bysilica gel using flash column chromatography (40:60 hexane/AcOEt) to give the MBH product 4a(31.0 mg, 94percent yield)

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ramireddy, Naresh; Zhao, John C.-G.; Tetrahedron Letters; vol. 55; 3; (2014); p. 706 – 709;,
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Application of 20780-72-7, 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 20780-72-7 as follows.

4-Bromoisatin 30 (1.00 g, 4.45 mmol), thiosemicarbazide (405 mg, 4.45 mmol) and K2CO3 (920 mg, 6.67 mmol) were suspended in water (50 mL). The reaction mixture was stirred at reflux for 16 h over which time the dark brown suspension became a clear light brown solution. The solution was carefully acidified by dropwise addition of acetic acid and resulting precipitate was filtered. The precipitate was recrystallised from DMF to yield the title compound (34) as a red solid (1.18 g, 95percent); mp (Gallenkamp) >300 °C; numax (solid) 3389 (br), 3297, 1604, 1573, 1140; deltaH (500 MHz, DMSO-d6, 363 K) 7.43-7.52 (3H, m, C(6)H, C(7)H), and C(8)H), 14.68 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 113.0, 117.0, 118.3, 127.4, 133.5, 136.1, 145.3, 149.9, 180.0; m/z (ESI-) 279 ([79BrM-H]-, 100percent), 281 ([81BrM-H]-, 100percent); HRMS (ESI-) C9H5BrN4S ([79BrM-H]-) requires: 278.9335; found 278.9343, ([81BrM-H]-) requires 280.9314; found 280.9320.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, category: indolines-derivatives

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6?10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Yellow solid, yield: 89percent, m. p.: 153.1?154.9°C, Rf=0.26 (petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.49 (t, J=8.0Hz, 1H), 7.33 (d, J=8.1Hz, 1H), 7.11 (d, J=7.9Hz, 1H), 4.57 (d, J=2.5Hz, 2H), 2.34 (t, J=2.5Hz, 1H).13C NMR (100MHz, CDCl3) delta 179.90, 156.21, 151.10, 138.42, 128.93, 121.74, 116.52, 109.86, 75.36, 73.67, 30.94, 29.53

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
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Application of 20780-72-7, 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.

Take 4-bromo indolone 1.0g (4.4mmol) into a 25mL round bottom flask,4 mL of N, N-dimethylformamide was added,Stirring to make it fully dissolved, and then adding 1.83 g (13.2 mmol) of anhydrous potassium carbonate,Further, 1.0 g (6.6 mmol) of methyl iodide was added.The reaction at room temperature for 8h, TLC detection of raw materials disappeared, adding 30mL of water,Then, the mixture was extracted with ethyl acetate (100 mL × 3), the combined organic phases were dried over anhydrous sodium sulfate,The solvent was decanted and the residue purified by petroleum ether: ethyl acetate = 10: 1200-300 mesh silica gel column.There was obtained 0.90 g of 1-methyl-4-bromoindodione in 85percent yield.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (12 pag.)CN104402794; (2017); B;,
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