Indolines-derivatives

Electric Literature of 496-12-8, 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 496-12-8 as follows.

A 1.0 g (8.4 mmol) amount of isoindoline was dissolved in 25 mL of acetonitrile. After addition of potassium carbonate (2.3 g, 16.8 mmol), the resulting mixture was heated at 70 C. After 30 min, the solution was allowed to cool to room temperature. A 4.2 mL (47.2 mmol) amount of 1-bromo-3-chloropropane was added and the reaction mixture stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3¡Á30 mL dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled collection of the product as a brown liquid (1.27 g, 77%). TLC: Rf 0.7 (DCM:MeOH(NH3), 9:1, v/v). 1H NMR (300MHz, CDCl3) delta: 7.21 (s, 4H, Haro); 3.95 (s, 4H, 2 CH2); 3.69 (t, 3J=7Hz, 2H, CH2); 2.90 (t, 3J=7Hz, 2H, CH2); 2.07 (p, 3J=7Hz, 2H, CH2). 13C NMR (75MHz, CDCl3) delta: 140.0 (2Caro); 126.7 (2Caro); 122.3 (2Caro); 59.1 (2CH2); 53.0 (CH2); 43.1 (CH2); 31.9 (CH2). LCMS (ESI+): Calc. for [M+H]: 196.05; 198.07. Found: 195.95; 197.91.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, 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 1168150-46-6, Computed Properties of C18H15NO4

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

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, (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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 6941-75-9 as follows. SDS of cas: 6941-75-9

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22120-50-9, name is 2,3-Dimethylindoline, 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 22120-50-9, Safety of 2,3-Dimethylindoline

A mixture of 2,3-dimethylindoline (0.10 g, 0.679 mmol) and 2-bromoethanamine hydrobromide(0.153 g, 0.747 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purifiedby preparative HPLC to give the title compound as a mixture of cis and trans ismoers that was notpurified further (128 mg). LCMS m/z = 191.2 [M+H]+.

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, 2,3-Dimethylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 56341-37-8, These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

Preparation of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl] ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one: (i) Preparation of 6-chloro-5-(chloroacetyl)oxindole : charge 250 ml of methylene dichloride and 100 gm of 6-chloro-oxindole in a 3 litre three neck flask under nitrogen atmosphere at 25 to 30C. Cool gradually to 0 to 5C under stirring and charge 199 gm of anhydrous aluminium chloride in portions at 0 to [50c] and stir for 15 min at 0 to 5C. Add 87.6 gm of chloroacetyl chloride slowly at 0 to 5C over 30 mins. Stir at 0 to 5C for 30 mins. Heat the reaction mixture slowly to reflux (40 to 45C)] over 30 mins. Reflux for 12 hrs. On completion of reaction cool the reaction mixture to 25 to 30C, pour into 1 kg ice, 50 ml of conc. HCl and 450 ml of demin water at 0 to 10C under stirring over 30 mins. Stir for 30 mins, filter solid product and wash with demin water. Prepare a slurry of the solids in hexane and suck dry the product. Dry the product at 70 to 75C.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2003/99198; (2003); A2;,
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 334952-09-9 as follows. category: indolines-derivatives

Example 39 COMPOUND IN-031 3-[5-(2-Morpholin-4-yl-ethoxy)-1H-indol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 5-(2-morpholin-4-yl-ethoxy)-1HH-indole-2-carbaldehyde to give the title compound.

According to the analysis of related databases, 334952-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); A1;,
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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 7699-18-5

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

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; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

Step-a: 5-nitroindolin-2-one: To a stirred solution of oxindole (20 g, 150.21 mmol) in 100 mL of concentrated H2S04 at -15C was added fuming HN03 (9.47 g, 150.206 mmol) dropwise and maintained the reaction temperature at -15C. After completion of addition, the mixture was stirred for 30 min and then poured into ice water. A yellow precipitate was formed which was isolated by filtration (13 g, 48%). -NMR (300 MHz, DMSO-ito): delta 11 (s, 1H), 8.2 (d, 1H), 8.1 (s, 1H), 7.0 (d, 1H), 3.6 (s, 2H).

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; UJJINAMATADA, Ravi Kotrabasaiah; HOSAHALLI, Subramanya; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; WO2015/92118; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, 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.

Preparation 63: 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-isoindol-1 – one (1578) (1579) A stirred mixture of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (780 mg, 3.68 mmol), (1580) bis(pinacolato)diboron (1.089 g, 4.28 mmol) and potassium acetate (1.26 g, 12.87 mmol) anhydrous 1 ,4-dioxane (12 mL) was degassed with nitrogen for 5 minutes. 1 ,1′- bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (150 mg, 0.18 mmol) was then added and the reaction heated under nitrogen at 100C for 16 hours. After cooling to room temperature the mixture was diluted with water and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under vacuum to yield the title compound (1.1 g, 115 %) which was used crude without purification. MS: [M+H]+ = 260.

Statistics shows that 6-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 675109-26-9.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A solution of 6 g (0.05 mol) of 4-aminophenol in a mixture of 50 mL of water and 15 mL of 32% hydrochloric acid was cooled on an ice bath to 0C. At continuous stirring maintaining the temperature below 5C a solution was added of 4 g (0.055 mol) of sodium nitrite in 15 mL of water. The obtained solution of a diazonium salt was stirred for 40 min. It was then added to a cooled to -5C solution of tin(II) chloride obtained by dissolving 30 g of tin in a mixture of 50 mL of water and 100 mL of 32% hydrochloric acid. After stirring for 2 h to the reaction mixture was added a solution of 0.05 mol of an appropriate isatin in a sufficient amount of 2-propanol, also a solution was added of 6 g (0.07 mol) of sodium acetate in 35 mL of water. The mixture obtained was stirred for 2 h, heated to 50C, and left standing for crystallization. The separated precipitate was filtered off and several times washed with water on the filter. The filtrate was additionally diluted with water, the separated precipitate was filtered off, washed with water on the filter, the precipitates were combined and dried.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Murashevich; Nichik; Zamyatina; Toropin; Burmistrov; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 650 – 654; Zh. Org. Khim.; vol. 52; 5; (2016); p. 665 – 669;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem