Tag: M.W=200-300

Synthetic Route of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a suspension of intermediate 6 (0.2mmol) in anhydrous EtOH (30mL) was added different substituent (0.2mmol). The mixture was continually stirred under 50C for 2~3h until no starting material. Then the solvent was evaporated by rotary evaporation. The residue was purified by flash chromatography to afford compounds 7a-n.

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-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Hongling; Wang, Haijun; Wang, Jing; Lin, Yu; Ma, Yukun; Bu, Ming; Steroids; vol. 153; (2020);,
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Reference of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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.

0.4 mmol of 4,7-dichloropurine, 0.2 mmol of antipyrine and 1 mL of water were mixed, and stirred under an oil bath at 100 C for 48 hours, and then the resulting reaction system was sequentially cooled to room temperature, filtered, washed with water and dried under vacuum ( 0.005 MPa, 80 C, 10 h) gave the title compound I-3 (yellow solid, yield 88%, purity 99.8%).

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); 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. 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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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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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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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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 2058-72-2, SDS of cas: 2058-72-2

A mixture of 5-methoxy-N-methylisatin 1b (0.17g, 0.90mmol) and tryptamine (2) (0.16g, 1.00mmol) in EtOH (5mL) in the presence of glacial acetic acid (0.2mL) and 4A molecular seive were stirred at room temperature for 24h. The reaction mixture was filtered and washed with EtOH. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane:EtOAc (2:1) as an eluent to give spiro 3b (0.26g, 87%) as beige solid; m.p. 243-245C (lit. [25] 255-256C); 1H NMR (300MHz, CDCl3) delta 2.98 (t, J=5.7Hz, 2H, CH2), 3.25 (s, 3H, CH3), 3.34 (dt, J=5.4, 13.2Hz, 1H, CH2), 3.72 (s, 3H, OCH3), 3.88 (dt, J=6.3, 13.2Hz, 1H, CH2), 6.81-6.91 (m, 3H, ArH), 7.08-7.19 (m, 3H, ArH), 7.29 (br s, 1H, NH), 7.57 (d, J=5.9Hz, 1H, ArH); 13C NMR (75MHz, CDCl3) delta 22.0, 26.6, 40.0, 55.9, 62.0, 109.4, 111.2, 111.6, 111.9, 114.7, 118.4, 119.4, 122.3, 127.0, 129.9, 132.7, 136.4, 136.9, 156.6, 176.7.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Rattanopas, Sopita; Piyanuch, Pornthip; Wisansin, Kawintip; Charoenpanich, Adisri; Sirirak, Jitnapa; Phutdhawong, Waya; Wanichacheva, Nantanit; Journal of Photochemistry and Photobiology A: Chemistry; vol. 377; (2019); p. 138 – 148;,
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Reference of 6326-79-0, 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.

Synthesis of 1-Methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one (R7) Step 1: Synthesis of Intermediate I-4.1 [0293] To R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; US2014/275114; (2014); A1;,
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5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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: 5332-26-3

To a solution of diisopropylamine (2.33 g, 23.0 mmol) in THF (35 mL) at -78 C. was added n-butyllithium (21.2 mmol, 13.3 mL of a 1.6 M solution). After stirring for 15 min, the imine (4.0 g, 17.7 mmol) from reaction (31a) in THF (20 mL) was added dropwise. The mixture was allowed to stir for 1 h. N-(Bromomethyl)phthalimide (5.1 g, 21.2 mmol) was dissolved in THF (20 mL) and was added dropwise to the enolate. After stirring for 1 h at -78 C., the reaction was warmed to rt overnight. The reaction was quenched with water (2 mL) and the mixture concentrated under reduced pressure. The remaining residue was treated at 0 C. with 1 M hydrochloric acid/methanol (100 mL) for 20 min followed by warming to rt for an additional 40 min. After removing the methanol in vacuo, the water layer was neutralized with sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried and concentrated to give the desired amine (2.6 g, 57%). MS found: (M+H)+=263.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
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