Category: indolines-derivatives

Synthetic Route of 2913-97-5, A common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

To a solution of Example 32A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2 mL). The resulting solution was stirred for 3 hrs at 25° C. and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution extracted with aq. NaHCO3 (2.x.300 mL). Evaporation and purification of the organic layer gave 12.9 g of the title compound.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flentge, Charles A.; Chen, Hui-Ju; DeGoey, David A.; Flosi, William J.; Grampovnik, David J.; Huang, Peggy P.; Kempf, Dale J.; Klein, Larry L.; Krueger, Allan C.; Madigan, Darold L.; Randolph, John T.; Sun, Minghua; Yeung, Ming C.; Zhao, Chen; US2005/131042; (2005); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A solution of isatins 1 (0.6 mmol), dienones 2 (0.4 mmol) and proline, thioproline or sarcosine(0.8 mmol) in the 10.0 mL of EtOH at reflux for 3 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc=5:1~3:1) were carried out to furnish the corresponding products 3-5.

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:
Article; Lin, Bing; Zhou, Gen; Gong, Yi; Wei, Qi-Di; Tian, Min-Yi; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Molecules; vol. 22; 4; (2017);,
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Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, 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 7147-90-2, SDS of cas: 7147-90-2

General procedure: Phthalic anhydride or its derivatives (2.0 mmol) and 4-aminobutyric acid (2.0 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h. The reaction was quenched with water (10 mL) and was adjusted to pH 6-8 with NaOH (0.1 mol/L). The mixture was extracted with dichloromethane (10 mL × 3), and the organic layer was washed with aq. NaHCO3, and water and then evaporated to afford intermediate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloroisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Wu, Hongna; Wu, Jun; Zhang, Wenxuan; Li, Zhongwen; Fang, Jinhui; Lian, Xu; Qin, Tong; Hao, Jie; Zhou, Qi; Wu, Song; Bioorganic and Medicinal Chemistry Letters; vol. 29; 7; (2019); p. 870 – 872;,
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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;,
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Synthetic Route of 99365-40-9,Some common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

6-(Furan-2-yl)-oxindole 6-Bromo-oxindole (0.40 g, 1.88 mmol), 2-tributyltinfuran (0.71 ML, 2.26 mmol), and tetraethylammonium chloride hydrate (0.31 g, 1.88 mmol) were combined and dissolved in acetonitrile (15 ML).. The palladium catalyst, bistriphenylphosphinedichloropalladium (II) (0.66 g, 0.09 mmol) was added and the reaction was warmed to 85 C. under nitrogen for 20 h.. The reaction was cooled to room temperature and diluted with water (15 ML) before passing the mixture through celite.. The pad of celite was washed with EtOAc and the filtrates were combined and separated.. The aqueous layer was washed with EtOAc (2*20 ML each).. The combined organic phases were washed with brine and dried over sodium sulfate.. The volatiles ere removed in vacuo.. The resulting residue was triturated with diethyl ether and the solid was collected by filtration (0.13 g, 34%). 1H NMR 300 MHz (DMSO-d6) delta 10.5 (s, 1H); 7.75 (s, 1H); 7.30 (m, 2H); 7.11 (s, 1H); 6.91 (m, 1H); 6.60 (m, 1H); 3.52 (s, 2H).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
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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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H4BrNO2

To a solution of compound 10 (10 g, 44.24 mmol) inEtOH (130 mL) was added a solution of hydroxylamine hydrochloride(4.61 g, 66.34 mmol) in H2O (20 mL) and the mixture was stirred at 80 C for 12 h. The mixture was concentrated under reduced pressure and the solid formed was filtered, washed with cold water, and dried under high vacuum to afford 10.24 g (96%) of compound 11 as a blood-red solid. IR (KBr) max. cm-1: 3336, 3330 (NH2), 3310 (OH),3038 (Ar-H), 2920 (Alph-H), 1690 (C=O), 1612, 1515, 1414(C=C), 1260 (C-N). 1H NMR (500 MHz, DMSO-d6) =7.02 (s, 1H, H-7); 7.20 (d, 1H, J = 8.2 Hz, H-5); 7.84 (d, 1H,J = 8.1 Hz, H-4); 10.83 (s, 1H, NH); 13.49 (s, 1H, OH); 13CNMR (125.7 MHz, DMSO-d6) = 113.12 (aromatic-C),115.50 (aromatic-C), 124.84 (aromatic-C), 128.46 (aromatic-C), 143.48 (aromatic-C), 144.02 (aromatic-C), 164.29,167.12 (C=O). Calculated (%) for C8H5BrN2O2 (239.95); C:39.86, H: 2.09, N: 11.62, found (%); C: 39.80, H: 2.14, N:11.58.

According to the analysis of related databases, 6326-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ullah, Nisar; Medicinal Chemistry; vol. 10; 5; (2014); p. 484 – 496;,
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Electric Literature of 7699-18-5, The chemical industry reduces the impact on the environment during synthesis 7699-18-5, name is 5-Methoxyindolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: The appropriate indolin-2-one (10 mmol) was dissolved in methanol (100 mL) and treated with the equivalent of the appropriate imidazo[2,1-b]thiazole-5-carbaldehyde 2 and piperidine (1 mL toobtain compounds 6, 8, 10) or 37% hydrochloric acid (1 mL to obtain compounds 7, 9). The reaction mixture was refluxed for 8-13 h (according to a TLC test), and the precipitate formed on cooling was collected by filtration.

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-Methoxyindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Conti, Ilaria; Morigi, Rita; Locatelli, Alessandra; Rambaldi, Mirella; Bua, Gloria; Gallinella, Giorgio; Leoni, Alberto; Molecules; vol. 24; 6; (2019);,
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Reference of 1127-59-9, These common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-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: 0.31 g (1.1 mmol) of 3,5-di-tert-butyl-4-hydroxybenzyl acetate 14 and 0.03 mL of triethyl-amine were added to a continuously stirred solution of the isatin derivative 1?13 (1 mmol) in DMF. The reaction was performed at 70°, completion of the reaction of the reactants was determined by TLC. After cooling to ambient, the reaction mixture was poured into a brine. The obtained precipitate was filtered off, washed with water, and dried in vacuum (12 mmHg).

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bogdanov; Zaripova; Voloshina; Strobykina; Kulik; Bukharov; Mironov; Russian Journal of General Chemistry; vol. 88; 1; (2018); p. 57 – 67; Zh. Obshch. Khim.; vol. 88; 1; (2018); p. 61 – 71,11;,
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Related Products of 17702-83-9, 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. 17702-83-9 name is 2-(8-Bromooctyl)isoindoline-1,3-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.

A mixture of 2-(8-bromodecyl)isoindoline-1 ,3-dione (0.91 g, 2.70 mmol) and tris(4- methoxyphenyl)phosphine (1 g, 2.84 mmol) in MeCN (10 mL) was heated at 70 °C overnight. On cooling the solvent was removed in vacuo and the resulting residue purified by column chromatography eluting with 10percent MeOH in DCM to give [8-(1 ,3-dioxo-2,3-dihydro-1 H- isoindol-2-yl)octyl]tris(4-methoxyphenyl)phosphonium bromide (1.56 g, 82percent) as a white foam. [00283] 1 H NMR (Method A) (DMSO-d6): delta (delta) ppm 7.88-7.81 (4H, m), 7.65 (6H, m), 7.28 (6H, m), 3.88 (9H, s), 3.54 (2H, t), 3.31 (2H, m), 1.61 -1 .36 (6H, m), 1.23 (6H, m); 31 P NMR (162 MHz, DMSO-de): delta (delta) ppm +21 .7 ppm; LC-MS (Method G) 610 [M]+; RT 2.13 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(8-Bromooctyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; NOVINTUM BIOTECHNOLOGY GMBH; SPAREY, Tim; RATCLIFFE, Andrew; STEVENSON, Brett; LAGASSE, Franz; COCHRANE, Edward; FROIDBISE, Alexandre; LASSALLE, Gilbert; (120 pag.)WO2018/193126; (2018); A1;,
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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;,
Indoline – Wikipedia,
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