Month: March 2021

Synthetic Route of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-39-0, These common heterocyclic compound, 56341-39-0, name is 6-Fluoroindolin-2-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.

EXAMPLE 13 A solution of 6-fluorooxindole (264 mg, 1.75 mmol), (prepared according to Synthesis 1993, 51), in THF (3 ml) was added dropwise under nitrogen to sodium hydride (42 mg, 1.75 mmol, pre-washed with hexane). After stirring the resulting mixture for 20 minutes at ambient temperature, 4-chloro-6,7-dimethoxyquinazoline (210 mg, 0.93 mmol), (prepared as described for the starting material in Example 1), was added as a solid, followed by DMF (4 ml). The reaction mixture was then heated at 85 C. for 1 hour, the solvent was removed by evaporation and the residue partitioned between ether and water. The aqueous layer was separated and neutralised with 2M hydrochloric acid and the solid was collected by filtration, washed with ether and dried under vacuum to give 6,7-dimethoxy4-(6-fluorooxindol-3-yl)quinazoline (255 mg, 81%) as a yellow solid. m.p. 315 C. (decomposition) 1H NMR Spectrum: (DMSOd6, CF3CO2D) 3.85(s, 3H); 3.98(s, 3H); 6.75-6.9(m, 2H); 7.42(s, 1H); 7.65(m, 1H); 7.75(s, 1H); 8.75(s, 1H). MS: 340 [MH]+

Statistics shows that 6-Fluoroindolin-2-one is playing an increasingly important role. we look forward to future research findings about 56341-39-0.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Chloromethyl)isoindoline-1,3-dione

Preparation 14; 2-(l-lsopropyl-4-oxopiperidiii-3~ylmethyi)isomdole-l,3~dioj5e To a solution of diisopropylamine (3mL, 21.2mmol) in THF (15mL) at -78C under Ar was added w-butyl lithium (2.5M in hexanes, 8.5mL, 21.2mmol) before 0,25h later 1- isopropylpiperidin-4-one (2.5g, 17.7mmol) in THF (15mL) was added dropwise to the mixture. After stirring for a further Ih at -78C 2-chloromethylisoindole-l,3-dione (5.2g, 26.6mmol) in THF (30mL) was added dropwise. After Ih at -78? the mixture was warmed to ri, stirred for 16h before sat. NFLjCl solution (50mL) was added and the mixture extracted with EtOAc. The combined organic phase was washed with brine, dried (MgS04) and the solvent was removed in vacuo. The residue was purified by column chromatography (1 :199 NEt3:DCM to 1 :20: 179 NEt3:MeOH:DCM) to give, after removal of the solvent in vacuo, the title compound: RT=== 2.00mm; m/z (ES+) = 301.1 [M ? H]+.

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:
Patent; PROSIDION LIMITED; BLOXHAM, Jason; BRADLEY, Stuart Edward; SAMBROOK-SMITH, Colin Peter; SMYTH, Donald; KEILY, John; DAWSON, Graham John; RASAMISON, Chrystelle Marie; BELL, James Charles; WO2011/117254; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20870-90-0, These common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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.

5-bromo-1-methylindolin-2-one (500 mg, 2.21 mmcl) was dissolved in dry THF (5 mL). The solution was purged with N2 and Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added to the solution. The freshly prepared bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol) was added slowly as a solution in THF (approx. 0.8 M). The resulting mixture was heated at 70C for 1 h30. Partial conversion was obersved by LCMS. The mixture was heated at 70C overnight, no change in profile. Further Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added followed by bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol). Heating to 70C was continued until almost complete conversion was observed (1h30).The mixture was cooled to rt and was quenched with water and EtOAc. The mixture was filtered through a pad of Celite. After phases separation, the remaining organic layer was dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography eluting with a gradient of Cyclohexane/EtOAc from [100:0] to [65:35]. The product fractions were combined and concentrated to dryness to afford methyl 1-(1- methyl-2-oxo-2,3-dihydro-1 H-indol-5-yl)cyclopropane-1 -carboxylate Ex.75a (99 mg, 18%) as pale orange solid. 1H NMR (300 MHz, DMSO-d6, din ppm): 1.12- 1.16 (m, 2H), 1.44-1.48 (m, 2H), 3.09 (s, 3H), 3.51 (s, 2H), 3.52 (s, 3H), 6.88 (d, 1H, J=8.7Hz), 7.21 (d, 1H, J=1.8Hz), 7.23 (d, 1H, J=1.8Hz).

Statistics shows that 5-Bromo-1-methyl-2-oxoindoline is playing an increasingly important role. we look forward to future research findings about 20870-90-0.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Product Details of 102359-00-2

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

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; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 341988-36-1,Some common heterocyclic compound, 341988-36-1, name is Methyl indoline-6-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.

General working procedure GWP I-sulfonylation: A solution of the sulfonyl chloride C (1 equiv.) in dichloromethane was added at room temperature to a solution of the amino acid ester A (1.2 equiv.) and diisopropylethylamine (1 to 3 equiv.) in dichloromethane. The reaction mixture was stirred for 12 h at room temperature, then washed 3.x. with a 1N HCl solution, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (silica; ethyl acetate/-hexane) yielded the desired product.

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-6-carboxylate, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; US2010/234340; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-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 5332-26-3, Recommanded Product: 5332-26-3

To a solution of N-(bromomethyl)phthalimide (2.0 g, 8.3 mmol) in CH2Cl2 (15 mL) was added sodium azide (1.62 g, 24.9 mmol), tetrabutylammonium iodide (0.10 g, 0.33 mmol) and H2O (3 mL). The reaction mixture was heated at reflux for 24 h. The mixture was cooled at room temperature, CH2Cl2 (5 mL) was added and the organic phase was washed and dried over Na2SO4, the solvent was removed in vacuo and the product was purified by crystallisation to afford a yellow solid (1.6 g, 95%); m.p. 39-40 C (lit. 37-39 C);21 FTIR (ATR, cm-1): 3474, 2962, 2872, 2129, 1776, 1712, 1610; 1H NMR (300 MHz, CDCl3) delta 7.94 (dd, J = 5.5, 3.1 Hz, 2H), 7.80 (dd, J = 5.5, 3.1 Hz, 2H), 5.08 (s, 2H); 13C NMR (75 MHz, CDCl3) delta 167.1 (2 ¡Á C), 134.6 (2 ¡Á CH), 131.7 (2 ¡Á C), 123.9 (2 ¡Á CH), 52.2 (CH2); MS [EI+] m/z (%): 202 [M]+ (5), 173 [M – HN2]+ (10), 161 [C8H5N2O2] (10), 159 [M – HN3]+ (40), 147 [C8H5NO2] (10), 133 [C8H5O2] (60), 104 [C7H4O] (100).

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

Reference:
Article; Lopez-Gonzalez, Ricardo; Bautista-Renedo, Joanatan; Martinez-Otero, Diego; Reyes, Horacio; Gonzalez-Rivas, Nelly; Cuevas-Yanez, Erick; Journal of Chemical Research; vol. 40; 5; (2016); p. 308 – 313;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-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 39603-24-2, Computed Properties of C10H9NO2

General procedure: To a solution of isatin 1 (0.5 mmol) in THF (2 mL) was added quinine (0.017 g, 10 mol%). The mixture was cooled to -78 C and stirred at this temperature for 15 minutes. Then the solution of 2-(trimethylsilyloxy)furan 2 (0.156 g, 1 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 C for 15 minutes. The reaction was monitored by TLC. After the completion ofthe reaction it was quenched by addition of 10% aqueous HCl (2.0 mL) and the mixture wasextracted with ethyl acetate (3¡Á5 mL). The combined organic layer was washed with brine solution,dried over MgSO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (AcOEt/hexane) to afford the product as a white 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:
Article; Kong, Shasha; Fan, Weidong; Lyu, Hairong; Zhan, Junchen; Miao, Xinyu; Miao, Zhiwei; Synthetic Communications; vol. 44; 7; (2014); p. 936 – 942;,
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., SDS of cas: 1074-82-4

(k) Preparation of 3-phthalimidylpropanol (compound 106) 3-Bromopropanol (4.0 g, 28.78 mmol), potassium phthalimide (8.0 g, 43.17 mmol) and potassium carbonate (4.0 g, 28.78 mmol) were added to 20 mL DMF. The reaction mixture was stirred at 70 C. for 4 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, saturated NaCl solution and evaporated in vacuo to a solid which was crystallized in ethyl acetate (3.5 g, 67%).

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; CytoMed Incorporated; US6201016; (2001); B1;; ; Patent; Cytomed, Inc.; US5681966; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem