Author: tianli

88784-33-2, A common heterocyclic compound, 88784-33-2, name is (S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid, molecular formula is C20H17NO6, 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.

a (1S-cis)-Octahydro-9-phthalimido-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 1,1-dimethylethylester 5,6-Dihydro-1,3(2H,4H)-pyridazinedicarboxylic acid, 3-(1,1-dimethylethyl)-1-(phenylmethyl)ester [prepared as described by Adams et al., Synthetic Communications, 18(18), 2225-2231 (1988)] was reacted with (S)-2-phthalimidopentanedioic acid, 5-(phenylmethyl) ester according to the procedure described by Attwood et al.(J. Chem. Soc. Perkins Trans I, 1986, p. 1011-1019) affording (S)-2-[2-phthalimido-1,5-dioxo-5-(phenylmethoxy)pentyl]-5,6-dihydro-1,3(2H,4H)-pyridazinedicarboxylic acid, 3-(1,1-dimethylethyl)-1-(phenylmethyl) ester.

The synthetic route of 88784-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5552397; (1996); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

Statistics shows that 15362-40-0 is playing an increasingly important role. we look forward to future research findings about 1-(2,6-Dichlorophenyl)-2-indolinone.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, 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 3416-57-7. 3416-57-7

A 20-mL Schlenk replaced with argon was cooled to 0 C. in an ice bath, and methanol (5 mL), methylene chloride (5 mL), phthalsuccinimidyl acetone 2 (MW: 203.19) (406.4 mg), (R)-1-phenylethylamine (MW: 121.18) (283.6 mL), and formic acid (MW: 46.03) (226.4 mL) were added. (S)-Catalyst 1 (MW: 562.15) (5.65 mg) was added thereto, and the mixture was stirred with heating at 30 C. for 16 h. After 16 h, 1H-NMR spectrum was measured to confirm the generation of desired product with a conversion rate of 63%. Regarding the diastereomer ratio, generation of a single diastereomer (>99% de) was confirmed in H-NMR spectrum in deuterated chloroform.

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 2-(2-Oxopropyl)isoindoline-1,3-dione.

Reference:
Patent; Kanto Kagaku Kabushiki Kaisha; Watanabe, Masahito; Takemoto, Toshihide; Tanaka, Kouichi; Murata, Kunihiko; (36 pag.)US2016/60282; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

52351-75-4, Adding a certain compound to certain chemical reactions, such as: 52351-75-4, name is 6-Methoxyindoline-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 52351-75-4.

6-Methoxylisatin (6 g, 33.87 mmol), 1 -indan-ethanone (40.64 mmol), and o 85% KOH pellets (120 mmol) were dissolved in EtOH (40 mL). The reaction mixture was stirred at 800C for 24 hours. After the solvent was removed by evaporation, the residue thus obtained was dissolved in H2O (50 mL). The solution was then washed twice with Et2O (30 mL). The aqueous phase was cooled by an ice- water bath and acidified with a 37% HCl aqueous solution to pH 1. The precipitate was collected by suction filtration, washed with H2O, and dried to give compound I- 20, 2-indan-5-yl-7-methoxy-quinoline-4-carboxylic acid (9.5 g, 88%) as a solid. ESI- MS (M+H+) = 320.

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, 6-Methoxyindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIGEN BIOTECHNOLOGY CO. LTD.; WO2008/95058; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, 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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below.

Butyllithium (2.5 M in hexanes, 3.76 mL, 9.39 mmol) was added to a solution of oxindole (500 mg, 3.76 mmol) at -78 0C in TEtaF (40 mL). After complete addition, NJSfJSf1N- tetramethylethane-l,2-diamine (1.48 mL, 9.76 mmol) was added, maintaining the internal temperature < 70 0C. After 1 h at -78 0C, 2-iodoethyl ether (4.90 g, 15.0 mmol) was added and the reaction warmed to ambient temperature. After 48 h the reaction was quenched with H2O (5 mL) and the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous solution was extracted with EtOAc (3 x 50 mL) and the combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of CH2Cl2MeOH- 100:0 to 97:3, gave the title compound. MS: m/z = 204 (M + 1). 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; MERCK & CO., INC.; WO2006/31610; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3484-35-3, Name is 5-Methylindolin-2-one, 3484-35-3, 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.

General procedure: To a solution of s7 (398 mg, 1.18 mmol) in EtOH (2.30 mL) were successively added addedoxindole (105 mg, 1.13 mmol) and piperidine (12 muL, 0.12 mmol) at room temperature. After 20 h,the reaction mixture was concentrated in vacuo. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 4/1) to afford aldehyde 1a (422 mg, 84%) as yellowsolid, whose geometry was determined by X-ray crystal analysis.

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3484-35-3, name is 5-Methylindolin-2-one, 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. 3484-35-3

General procedure: A mixture of compound 4 (10 mmol), benzaldehyde (12 mmol) and afew drops of piperidine in ethanol (100 mL) was refluxed for 2 h. Partof the solvent was evaporated under reduced pressure and the residue was cooled to room temperature to crystallise the solid product,which was filtered off, washed twice with ethanol, and dried to yield compound 5.

Statistics shows that 3484-35-3 is playing an increasingly important role. we look forward to future research findings about 5-Methylindolin-2-one.

Reference:
Article; Jiang, Hongwu; Feng, Zhiyuan; Chen, Taiping; Li, Zicheng; Huang, Wencai; Luo, Youfu; Zhao, Yinglan; Journal of Chemical Research; vol. 42; 1; (2018); p. 44 – 49;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 39755-95-8, name is 5-Methoxyisatin, 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 39755-95-8. 39755-95-8

Synthesis of l -Benzyl-5-methoxyindolin-2-one[00143] A stirred solution of 5-methoxyisatin (5.0 g, 28 mmol) in dry DMF (40 mL) was cooled in an ice bath before addition of sodium hydride (60 wt% in mineral oil, 1.7 g, 42 mmol) slowly, the dark red solution turning quickly black. After stirring for 20 min, BnBr (3.7 mL, 31 mmol) was added to the reaction mixture by syringe and the resulting mixture was stirred for 1 h. Water (150 mL) was added with stirring, and the resulting dark red precipitate collected by filtration and washed with water to give l-benzyl-5- methoxyindoline-2,3-dione as a dark red solid (6.1 g, 81%). NMR (400 MHz, CDC13) delta 7.39-7.31 (m, 5H), 7.17 (s, 1H), 7.03 (d, J = 8.1 Hz, 1H), 6.68 (d, J = 8.6 Hz, 1H), 4.92 (s, 2H), 3.79 (s, 3H). MS ESI 268.1 [M + H]+, calcd for [C16H13N03+ Hf 268.09.

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 5-Methoxyisatin.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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: Method A: To a stirred suspension of the appropriate nitrogen derivative II (0.16 mmol) and chlorophosphine gold(l) compound III (0.16 mmol) in MeOH (2 mL) was added dropwise NaOMe (0.5 M in MeOH , 0.18 mmol). The reaction was stirred at rt for 16 h before concentrating in vacuo to give a solid residue which was suspended in DCM (2 mL) and filtered. The filtrate was concentrated in vacuo giving an oily residue which after trituration with Et.20 (x 3) and drying under high vacuum for 16 h, provided the title compound I. Method E: As Method A except the reaction mixture was heated at 50 C for 18 h.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AUSPHERIX LIMITED; HOLMES, Ian; NAYLOR, Alan; ALBER, Dagmar; POWELL, Jonathan Raymond; MAJOR, Meriel Ruth; NEGOITA-GIRAS, Gabriel; ALLEN, Daniel Rees; GUETZOYAN, Lucie Juliette; KING, Nigel Paul; CHAPMAN, Nicholas Andrew; (155 pag.)WO2017/93545; (2017); 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 100487-74-9 as follows. 100487-74-9

Preparation 29 6-Chloro-5-fluoro-indole To a solution of 6-chloro-5-fluoro-oxindole (0.49 g, 2.64 mmol) in THF (5 mL) was added slowly 1M BH3 in THF (21.2 mL, 21.2 mmol) over 30 minutes. The mixture was stirred 24 hours and 1N aqueous NaOH (25 mL) was added carefully with stirring. After stirring 20 minutes the mixture was extracted with EtOAc/Et2 O (1:1), and the extracts were combined, washed with brine, dried over Na2 SO4(s), filtered and concentrated in vacuo to afford 412 mg of the product as a mixture of 6-chloro-5-fluoroindole and 6-chloro-5-fluoroindoline (GC-MS: 169, and 171 (M+), respectively),which was used without further purification.

According to the analysis of related databases, 100487-74-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem