Month: January 2021

Electric Literature of 1168150-46-6, A common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, molecular formula is C18H15NO4, 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.

N-methyl-2-(4-methylpiperazin-1-yl)-N-(5-amino-2-yl)acetamide (466m9,1.6mmo1) and (E) -3- (methyl group (phenyl) methylene) -2-oxo-indoline-6-carboxylate (500mg, 1.6mmol) placed in 15mL of methanol was heated to 70 C, 13h of holding, and then cooled to room temperature, washed with suction, the product of cold ethanol, and dried to give a bright yellow solid, methyl (Z)-3-((4-(N-cyclopropyl-2-(4-methylpiperazin-1-yl)acetylamino)anilino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (500mg, 80%).

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-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. Application In Synthesis of 2-(3-Oxobutyl)isoindoline-1,3-dione

Prepare a cold (0C) solution OF 2- (3-OXOBUTYL) ISOINDOLE-1, 3-dione (6. 8 g, 31.5 mmol) in methanol (50 mL). Add Br2 (3.2 mL, 63 MMOL). Allow the reaction to warm to room temperature and stir for 15 hours. Add 10 M sulfuric acid (26 mL) and stir the mixture for 15 hours. Filter off the solids and dry in vacuo to afford 2- (4-BROMO-3- oxobutyl) ISOINDOLE-1, 3-dione (2.3 g). 1H NMR (CDCl3) 8 7.85-7. 90 (m, 2H), 7. 69-7.77 (m, 2H), 4.05 (t, J= 7 Hz, 2H), 3.96 (s, 2H), 3.15 (t, J= 7 Hz, 2H).

The synthetic route of 2-(3-Oxobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/9941; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 stirred solution of tert-butyl 5-bromoisoindoline-2-carboxylate (32-1) (300 mg, 1.00 mmol) in dioxane and water (2.5 ml), was added 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridine (25-1) (459 mg, 1.10 mmol) and potassium phosphate (636 mg, 3.00 mmol) at room temperature. The reaction mixture was purged with argon for 5 minutes followed by addition of Pd(dppf)Cl2-DCM (40.8 mg, 50.0 mumol) at room temperature. The reaction mixture was heated to reflux overnight. After completion of reaction (monitored by TLC Rf = 0.4 in 20% ea/ hexane and LCMS), the reaction mixture was filtered and concentrated. The crude residue was purified by flash column (elution with 15 % EtOAc/Hexanes) to afford tert-butyl 5-(2,6- bis(benzyloxy)pyridin-3-yl)isoindoline-2-carboxylate (32-2) (330 mg, 648 mumol, 64.9 %) as a gummy liquid.1H NMR (400 MHz, DMSO-d6) delta 7.65-7.63 (m, 1H), 7.45-7.44 (m, 2H), 7.40-7.38 (m, 2H), 7.36-7.21 (m, 7H), 7.19 (m, 1H), 6.54 (m, 1H), 5.37 (br s, 4H), 4.63-4.60 (m, 2H), 4.43 (br s, 2H), 1.44-1.39 (m, 9H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 552330-86-6, name is 5-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. Application In Synthesis of 5-Bromoisoindolin-1-one

[0264] 5-Bromo-2,3-dihydro-isoindol-l-one (l.OOg, 4.72mmol), l-bromomethyl-4-methyl-benzene (1.14g, 6.14mmol) and cesium carbonate (3.08g, 9.44mmol) were suspended in anhydrous NMP (lOmL). The mixture was immersed in a 60C oil bath for 16.5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Column chromatography (20% to 40% ethyl acetate/hexanes) provided the title compound as a yellow solid (1.18g, 79%). 1H NMR CDC13: 7.76 (d, 1H), 7.62 (d, 1H), 7.55 (s, 1H), 4.76 (s, 2H), 4.24 (s, 2H), 2.35 (s, 3H).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1074-82-4

(0184) 3 (0185) A mixture of potassium pthalimide (10.0 g, 54.0 mmol) and 1 ,6-dibromobutane (9.97 ml_, 64.8 mmol) in dry DMF (100 ml_) was stirred at room temperature for 12 days. The mixture was concentrated and extracted with chloroform (3×30 ml_) and washed with deionised water (3x 80 ml_) and brine (100 ml_). The organic layer was dried over magnesium sulfate and concentrated to give a white syrup. The syrup was triturated with hexanes, filtered and dried to give a white solid product (3) (14.3 g, 85%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1074-82-4.

Reference:
Patent; SEREN TECHNOLOGIES LIMITED; NOCKEMANN, Peter; BROLLY, Donnacha; BRADLEY, Ena; MCCOURT, Eadaoin; (58 pag.)WO2019/239150; (2019); A1;,
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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 2-oxoindoline-6-carboxylate

Sodium hydroxide solution (1N, 20 ml) was added to a solution of methyl 2-oxoindoline-6-carboxylate (2 g, 10.46 mmol, 1.00 equiv) in methanol (20 ml). The resulting solution was stirred for 2 hours at 80 C. The reaction mixture was cooled to 30 C., diluted with 50 ml of H2O and extracted with 2*30 mL of dichloromethane. The aqueous layers were combined and the pH adjusted to 2 with aqueous hydrochloric acid (6 N). The solids were collected by filtration and dried to give the title product 1.28 g (69%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 12.86 (s, 1H), 10.50 (s, 1H), 7.55 (m, 1H), 7.32-7.30 (m, 2H), 3.56 (s, 2H).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
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 17564-64-6 as follows. Application In Synthesis of 2-(Chloromethyl)isoindoline-1,3-dione

A solution of ammonium O,O-(2-methylpentane-2,4-diyl) dithiophosphate (1) (0.01 mol) was dissolved in absolute methanol (20 mL) and treated with N-(chloromethyl)phthalimide (0.01 mol). The mixture was reuxed for 1 h, fltered and concentrated by distillation under reduced pressure.The resulting concentrated solution crystallized at room temperature. The white solid was fltered, washed with diethylether and dried over P2O5. It was recrystallized with aMeOH:CHCl3 (9:1) mixture. Color: white; yield: 75-80%,m.p. 66C. Anal. found C 48.98; H 4.82; N 3.93; S 17.51%.Calcd. for C15H18NO4PS2 (371.42): C 48.51; H 4.88; N 3.77; S17.27%; IR, flm nu(cm-1): = 1719 (C=O); 526 (P-S); 719 (P=S);1120 [(P)-O-C]; 967 [P-O-(C)]; 1H NMR: delta = 7.96 (m, 4H,Har); 4.99 (s, 2H, OCH2), 2.51 (s, 1H, OCH), 1.95 (s, 1H, CH),1.5 (m, 3H, CH3), 1.20 (m, 2H, CH2), 1.14 (m, 3H, CH3); 13CNMR: delta = 167.4 (C=O); 135.0 (C2); 131.5 (C3), 123.5 (C4); 86.9(N-CH2); 60.1 (OCH2); 72.6 (OCH); 128.3 (CH); 27.0 (CH3);31.5 (CH2); 21.6 (CH3), 31P NMR: delta = 82.9.

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rastogi, Rupali; Gupta, Srasti; Tarannum, Nazia; Agarwal, Ranu; Butcher; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 3; (2017); p. 300 – 306;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-2-one, 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 13220-46-7, name: 4-Methylindolin-2-one

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 ML of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours.. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products.. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours.. The solid was collected by vacuum filtration, washed with 20 ML of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds.. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid.. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid..

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Using the same procedure, N-(8-bromooctyl)phthalimide was converted to 2-[8-(1H-imidazol-1-yl)octyl]-1H-isoindole-1,3(2H)-dione, mp 43¡ã-45¡ã C.

The chemical industry reduces the impact on the environment during synthesis 2-(8-Bromooctyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Cyanamid Company; US4610981; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15937-07-2, name is 5,6-Dimethoxyindoline, 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 15937-07-2, HPLC of Formula: C10H13NO2

1st Stage 6.3 g of 4-nitrofluorobenzene (0.045 mol) were stirred with 8.0 g of 5,6-dimethoxyindoline (0.045 mol) and 4.2 g of sodium hydrogen carbonate (0.050 mol) for 2.5 h at 80 C. in 50 ml of DMSO. After cooling, the mixture was poured onto ice, the precipitate was removed by filtration under suction and the product was dried in vacuo at 45 C. The intermediate product 5,6-dimethoxy-1-(4-nitrophenyl)-indoline was obtained in a yield of 65.6% (melting point: 176-179 C.).

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, 5,6-Dimethoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Naumann, Frank; Hollenberg, Detlef; Hoeffkes, Horst; Rose, David; US2004/6834; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem