Month: April 2021

Application of 356068-93-4, 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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 7: Preparation of iV-(2-aminophenyl)-5-((Z)-(5-fluoro-2-oxoindolin- 3-ylidene)methyl)-2,4-dimethyl-lH-pyrrole-3-carboxamide (Compound 10)To a stirred solution of compound 109 (0.2 g, 0.67 mmol) in DMF (30 mL) at 00C was added etaOBt (0.136 g, 1.0 mmol), triethylamine (0.24 mL, 1.67 mmol), ECDI-etaC1 (0.192 g, 1.0 mmol) and benzene- 1,2-diamine (0.2 g, 2.0 mmol) successively. The mixture was stirred for 72 h at room temperature, diluted with water (20 mL), brine (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain the product 10 as a yellow solid (0.13 g, 50.03%). LCMS: 391 [M+lf, 1H NMR (DMSO-^6): delta 4.83 (s, 2H), 6.58 (t, J= 7.2 Hz, IH), 6.78 (d, IH), 6.84 (m, IH), 6.92 (t, J= 7.8 Hz, 2H), 7.25 (d, IH), 7.74 (m,2H), 9.00 (s, IH), 10.90 (d, IH) ,13.75 (s, IH), 1H NMR (DMSO-D2O) delta 2Al (s, 3H),2.44 (s, 3H), 6.62 (t, J= 7.4 Hz, IH), 6.78 (d, IH), 6.89 ( m, IH), 6.95 (m, 2H), 7.19 (d, IH), 7.67 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); 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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Product Details of 61-70-1

To a dried round-bottomed flask equipped with a magnetic stir bar was added 1-methylindolin-2-one (0.74 g, 5 mmol), Lawesson?s Reagent (1.07 g, 2.65 mmol) in dry CH2Cl2 (3.60 mL). The reaction was held at the room temperature for 20 h, followed by concentration in vacuo. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to get 1-methylindoline-2-thione 1 (0.69g, 85% bright yellow solid).

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; Zhou, Shiping; Xiao, Genhua; Liang, Yun; Tetrahedron Letters; vol. 58; 4; (2017); p. 338 – 341;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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. SDS of cas: 17564-64-6

2.5 g (38.4 mmol) of sodium azide was added to a solution of a commercially available N-(Chloromethyl)phthalimide (25.6 mmol, 5 g) in 50 mL of DMSO. The resulting suspension was stirred at room temperature for 24 h. After adding ice water, the mixture was extracted several times with diethyl ether. The combined organic phases were dried over MgSO4 and the solvent was removed by evaporation under vacuum. Azide 5 was sufficiently pure to be used thereafter (4.810 g, 93% yield).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ben Nejma, Aymen; Znati, Mansour; Daich, Adam; Othman, Mohamed; Lawson, Ata Martin; Ben Jannet, Hichem; Steroids; vol. 138; (2018); p. 102 – 107;,
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Reference of 32372-82-0, These common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, 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 stirred suspension of 4- (3-piperidin-1-ylpropoxy) benzoic acid hydrochloride (D2 (Method B); 25g) in DCM (250ML) at rt was treated with oxalyl chloride (10. 92MOL) and 10% DMF in DCM (1 drop). After 2h the solution was evaporated and then re- evaporated from DCM (100ML) and toluene (100ML). The acid chloride was redissolved in DCM (400MOI) and treated with isoindoline hydrochloride (12.8g). The stirred mixture was cooled in ice and triethylamine (46. 4ml) was added over 20min. The mixture was allowed to gain rt and stirred for 1 h. The solution was washed with saturated sodium hydrogen carbonate solution (2#200ML), water (2#200ML), brine (200MI), dried (MGS04) and evaporated. The residue was chromatographed on a silica gel flash column [step gradient 5-9% MEOH (containing 10%. 880 ammonia solution) in DCM]. Fractions containing the required product were evaporated and then re-evaporated from EtOH to give a solid (27.5g) which was redissolved in DCM (300ML), treated with 4M HCI in dioxan (28. 3ML) and then evaporated. The resulting solid was crystallised from EtOH/ diethyl ether to give 2 crops (28.5g). This material was recrystallised from MEOH/ diethyl ether to give the title compound (E2) (26.4g).

Statistics shows that Isoindoline hydrochloride is playing an increasingly important role. we look forward to future research findings about 32372-82-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/37788; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 50727-04-3, These common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-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.

A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSOd6) 7.13 (1 H, d), 6.84 (1H, d), 6.74 (1H, dd), 4.05 (2H, s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.

The synthetic route of 50727-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, 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. name: 2-(8-Bromooctyl)isoindoline-1,3-dione

General procedure: To a solution of compound 4 (2 mmol) in N,N-dimethylformamide (DMF) (40.0 mL), the intermediate 2 (0.44 g, 2.5 mmol) and KHCO3 (0.40 g, 4.0 mmol) were added. The mixture was heated at 35-40C for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel (VEtOAc-VPet = 2 : 3) to give compound 5. (Chart 1). The 1H-NMR data of compounds 5a-i were listed as follow.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
Indoline – Wikipedia,
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These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. Quality Control of 5-Methoxyindolin-2-one

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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 septum-capped vial with a stirring bar was charged with the corresponding isatin(0.1 mmol), ester (0.2 mmol, 2.0 equiv.), catalyst and solvent (1 mL). The reactionmixture was conducted in setting temperature and monitored by TLC. The resultingreaction mixture was vapored in vacuum and the residue was purified by columnchromatography (Hexane/EtOAc = 8/1 to 4/1). The desired products were obtained ascolorless oil or white solid.

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; Zhang, Xianhui; Zhou, Li; Mahmood, Qaiser; Zhao, Mengmeng; Wang, Xiaowu; Wang, Qinggang; Synlett; vol. 30; 5; (2019); p. 573 – 576;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: 1M solution of phenylmagnesium bromide in THF (20.40mL, 20.40mmol) was added dropwise to a stirred ice-cold solution of isatin (1g, 6.80mmol) in anhydrous THF (20mL) that was kept under nitrogen. The reaction was stirred at room temperature for 2h and then quenched with a saturated aqueous solution of NH4Cl (20mL). Water was then added (30mL) and the aqueous phase was extracted twice with dichloromethane (2¡Á60mL). The organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuum and the crude was purified by crystallization from EtOAc/Hexane to afford 1 (1.18g, 77.1%) as a white powder.

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; Denoyelle, Severine; Chen, Ting; Yang, Hongwei; Chen, Limo; Zhang, Yingzhen; Halperin, Jose A.; Aktas, Bertal H.; Chorev, Michael; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 537 – 553;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 114041-16-6, 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 114041-16-6 as follows.

A solution of 5,6-dimethoxyisoindoline 10e (0.08 g, 0.46 mmol) in acetic acid (0.92 mL) is stirred at room temperature. Sulfuryl chloride (0.11 mL, 1.4 mmol) is added drop-wise, and the resulting mixture is stirred at room temperature for 4 h. The reaction is concentrated under reduced pressure to give compound 10k as its HCl salt (0.130 g, quantitative yield) as a light-brown foam, m/z=248/250/252 [M+H]+.

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem