Category: indolines-derivatives

Application of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of the title A compound, 5-bromo-2, 3-DIHYDRO-1 H-INDOLE (15. 75 g, 79.54 mmol) in 200 mL acetonitrile and 200 mL dichloromethane is treated with DMAP (0.971 g, 7.95 mmol) and di-t-butyl dicarbonate (19.14 g, 87.49 MMOL). The solution is stirred at RT for 16 h. The mixture is diluted with 300 mL dichloromethane and washed twice with 1 N aqueous HCI and once with brine, dried over anhydrous MGS04, and concentrated to afford 5-bromo-2,3- dihydro-indole-1-carboxylic acid tert-butyl ester.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Preparation of Compound 29, 1-tert-butyl 5-methyl indoline-1,5-dicarboxylate[0044] Di-tert-butyl dicarbonate (0.489 g, 2.24 mmol), followed by triethylamine (0.315 mL, 2.24 mmol) was added to a solution of Compound 28 (0.328 g, 1 .85 mmol) in dry DCM (5.8 mL) and the reaction mixture was stirred at rt for 26 hrs, concentrated. The residue was dissolved in EtOAc and washed with water (1 x), brine (1 x), dried (MgS04), filtered and concentrated. The crude material was recrystallized from hot EtOH to afford the title compound (373 mg, 73%) as a white solid. 1H NMR (500 MHz, CDCI3) delta 7.88 (d, J = 7.6 Hz, 1 H), 7.82-7.79 (m, 1 H), 4.02 (t, J = 8.7 Hz, 2H), 3.88 (s, 3H), 3.14 – 3.09 (m, 2H), 1 .57 (br s, 9H). Note that there also appears to be 2 extremely broad and weak singlets centred at 7.85 and 7.50 ppm which may be the missing aromatic CH. LRMS (ESI+): 178.09 (loss of Boc) and very weak 278.15

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl indoline-5-carboxylate, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
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Electric Literature of 200049-46-3,Some common heterocyclic compound, 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-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.

To a solution of 1 -(3 -bromo- 1 -(tetrahydro-2H-pyran-4-yl)-6, 7-dihydro- 1H-pyrazolo[4, 3-c]pyridin-5(4H)-yl)ethanone (Intermediate H, 350 mg, 1.07 mmol) and bis(pinacolato)diboron(542 mg, 2.13 mmol) in dioxane (5.3 mL) was added KOAc (314 mg, 3.20 mmol), (2- dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) and 2-(dicyclohexylphosphino)- 2?,4?,6?-triisopropylbiphenyl (31 mg, 0.064 mmol). The mixture was stirred at 80C for 16 hunder a nitrogen atmosphere. The reaction mixture was cooled to room temperature and 7- bromoisoindolin-1-one (113 mg, 0.533 mmol), K3P04.H20 (313 mg, 1.33 mmol), water (1.3 mL) and (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) were added. The reaction mixture was stirred at 90 C for 4 h under a nitrogen atmosphere. The reaction mixture was thencooled to room temperature and concentrated in vacuo. The crude residue was dissolved indichloromethane (20 mL), dried over anhydrous MgSO4, filtered through celite and concentrated in vacuo. The mixture obtained was purified by silica gel chromatography (MeOH / iPrOAc = 1 10 to 1: 3) to give the title compound (144 mg, 36%) as a white solid. ?H NMR (400 IVIFIz, DMSO-d6, 23 / 24 H) 7.66 – 7.40 (m, 3H), 6.06 – 5.94 (m, 1H), 4.48 (d, J = 9.5 Hz, 2H), 4.62-4.41 (m, 1H),4.18(dd,J36.7, 11.6Hz,2H),3.99-3.77(m,2H),3.59-3.47(m,3H),2.82 (dt, J = 24.3, 5.9 Hz, 2H), 2.43 -2.30 (m, 2H), 2.17-2.06 (m, 3H), 1.93 (d, J = 13.2 Hz, 2H). LCMS M/Z (M+H) 381.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-2,3-dihydro-isoindol-1-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Indoline – Wikipedia,
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Synthetic Route of 923590-95-8, 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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-Bromoisoindoleline hydrochloride (174 mg, 0.74 mmol) and triethylamine (158.1 mg, 1.56 mmol) were added to a round bottom flask, DMF was dissolved, and stirred for 10 minutes.The final product 03 (80 mg, 0.25 mmol) was added and stirred at 50 C overnight.The reaction was completed and purified by HPLC to give 100 mg of a colorless oily compound.

The synthetic route of 4-Bromoisoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
Indoline – Wikipedia,
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Related Products of 56341-37-8, 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 56341-37-8 as follows.

6-CHLOROOXINDOLE (2.5 g, 14.9 MMOL) was suspended in 50 ml 4 M aqueous NAOH and the mixture was REFLUXED for 6 hours. The reaction mixture was allowed to cool and the product precipitated and filtered off with suction. The solid was dissolved in water (100 ml) and precipitated with 4 M aqueous HCI at 0C. The solid was then filtered with suction and dried under vacuum to yield 2.0 g (72%) of white crystalline solid. (2-Amino-4-chloro-phenyl)-acetic acid (700 mg, 3.8 MMOL) was then dissolved in 25 ML pyridine and 1-bromo-3-isocyanato-benzene (811 mg, 4.1 MMOL) was added drop-wise and the solution was stirred for 90 minutes. The reaction mixture was diluted with 150 ml ethyl acetate and washed twice with 1 M aqueous HCI. The organic phase was reduced under vacuum and the product recrystallised from ethyl ACETATE/HEPTANE to yield 680 mg of white crystalline solid (47%) (m. p. 195-196C)

According to the analysis of related databases, 56341-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROSEARCH A/S; WO2004/46090; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Formula: C8H4ClNO2

General procedure: To a solution of isatin 1 (1 mmol), nitromethane/nitroethane (3 mmol) was added DABCO (5 mol percent). The mixture was stirred at rt this temperature for 1-5 min. The reaction was monitered by TLC. After completion of the reaction, the mixture was extracted with ethyl acetate (3 .x. 5 mL). The combined organic layers were washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes: 30:70). All novel compounds were characterized by M.P., NMR, Mass and IR spectral data.

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

Reference:
Article; Meshram; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Tetrahedron Letters; vol. 52; 44; (2011); p. 5862 – 5864;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A solution of 123 g of pyridinium bromide perbromide in 600 ml of THF was slowly added dropwise to 2-(2-oxopropyl)-1H-isoindole-1,3 (2H)-dione (70 g; 0.345 mol) in 600 ml of THF, and the mixture was then stirred for about 3 h. For workup, the precipitated solids were filtered off, and the mother liquor was concentrated, taken up in ethyl acetate and thoroughly washed with aqueous bisulfite solution. Drying and concentration afforded 150 g of a yellow oil, which was stirred with methyl tert-butyl ether. 63.4 g; m.p.: 142 to 143 C.; ESI-MS [M+H+]=283.95

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott GmbH & Co. KG; US7105508; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

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; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H9NO2

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 39603-24-2 as follows. Quality Control of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of the compounds 11a-d (1 mmol) and substituted indolinone 15a-g (1.1 mmol) or appropriate aromatic aldehydes 12a-c (1.1 mmol) with catalyst amount of glacial acetic acid in ethanol (10 mL) was heated at reflux for 6 h and then cooled to room temperature and filtered. The obtained cake was washed with diethyl ether to get a white to light yellow solid. The crude product was purified by chromatography on silica gel using MeOH/CH2Cl2 to afford the desired compounds 16a-d and 17a-n.

According to the analysis of related databases, 39603-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bao, Guanglong; Du, Baoquan; Ma, Yuxiu; Zhao, Meng; Gong, Ping; Zhai, Xin; Medicinal Chemistry; vol. 12; 5; (2016); p. 489 – 498;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem