Month: June 2021

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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

(1) 1.33 g of 5-methylindoline and 2-chloropyridine were added to a 50 mL round bottom flask, the ratio of the amount of the substance was 1: 1.5; (2) Stir directly in the air and mix evenly at room temperature.Then heated at 80 C, after 45 min, the system solidified, stopped the reaction, and cooled to room temperature; (3) Add 50 mL of saturated NaHCO3 solution to the system to dissolve the solid.Further, 50 mL of ethyl acetate solution was added, shaken, and liquid-separated, and the aqueous phase was extracted three times with ethyl acetate, 30 mL each time, and the organic phase was combined and concentrated by a rotary evaporator; (4) The concentrate was dissolved in 20 mL of ethanol, refluxed at 80 C for 15 min, cooled, and a pale yellow solid was separated, filtered, rinsed with water and dried in vacuo to give the desired product.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Jiao Linyu; Zhang Ze; Yin Xiaomei; Hong Qian; Ning Zihui; Ma Xiaoxun; Li Zhuo; Sun Ming; (11 pag.)CN109265439; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 22 3- [2,4-Dimethyl-5-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 104 mg (64%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.38 (s, br, 1H, NH-1′), 12.02 (s, br, 1H, COOH), 10.57 (s, br, 1H, NH-1), 7.52 (s, br, 1H, H-4), 7.50 (s, 1H, H-vinyl), 6.87 (d, J=7.86 Hz, 1H, H-6), 6.73 (d, J=7.86 Hz, 1H, H-7), 2.63 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.28 (s, 3H, CH3), and 2.24 (s, 3H, CH3); MS m/z (relative intensity, %) 325 ([M+1]+, 66).

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-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 825-70-7, 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 825-70-7 as follows.

General procedure: to a suspension of iv (1mmol) in acetonitrile (10ml) was added 5-fluoroindoline (1.2mmol). The reaction mixture was stirred at 40C for 16h and then evaporated to dryness under reduced pressure. Water (10mL) and diethylether (15mL) were added and the resulting mixture was stirred for 5min. The precipitate formed was filtered off and dried to give 7 (86%) as a white solid.

According to the analysis of related databases, 825-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Filoche-Romme, Bruno; Carry, Jean-Christophe; Gruss-Leleu, Florence; Bertin, Luc; Guizani, Houlfa; Pilorge, Fabienne; Richepin, Patrick; Karlsson, Andreas; Charrier, Veronique; Abecassis, Pierre-Yves; Vincent, Loic; Nicolas, Jean-Paul; Lengauer, Christoph; Garcia-Echeverria, Carlos; Schio, Laurent; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1506 – 1510;,
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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6-Difluoroindoline-2,3-dione

The 5,6-difluoro isatin(1.83g, 10mmol)Add 10 mL of acetonitrile to a 100 mL round bottom flask.N-methylpiperazine (1.10 g, 11 mmol) was added dropwise, followed by stirring at room temperature for 4 h. After the reaction was monitored by TLC, purification by column chromatography gave a red solid with a yield of 48%.

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; Sun Yat-sen University; Huang Zhishu; Tan Jiaheng; Che Tong; (27 pag.)CN107540662; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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.

In the (G2a) step, 2 mol of thionylchloride (SOCl2) was added to the compound 1a to produce 2-(1,3-dioxoisoindolin-2-yl)acetic chloride (compound 2a) and the unreacted thionylchloride (SOCl2) was recovered by using an aspirator.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERMOLON KOREA CO.,LTD.; WO2009/131324; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime 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. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

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

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, name is Isoindoline, 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: 496-12-8

To a suspension of 2-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.50 g, 1.15 mmol) in anhydrous DMF (9 mL) was added isoindoline (0.41 mL, 3.46 mmol) and the reaction mixture was stirred at room temperature for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was triturated with water (50 mL). The separated solid was filtered, washed with water and ether, and dried under vacuum to give the title compound as a white solid. Yield: 0.45 g (83%). MP 202-202.5 C. 1H NMR (400 MHz, CDCl3): delta 10.09 (br s, 1H), 7.77 (s, 2H), 7.22 (br s, 4H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 4.11 (s, 4H), 4.03 (t, J=6.0 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.22 (t, J=6.0 Hz, 2H), 2.42 (s, 6H)

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 356068-93-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 356068-93-4 name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of compound 1 (0.5 g, 1.67 mmol) in DMF (35 rnL) at room temperature was added etaOBt (1.02 g, 7.52 mmol), triethylamine (2.12 mL, 15.03 mmol), ECDIetaC1 (1.44 g, 1.52 mmol) and methyl 6-aminohexanate hydrochloride(0.91 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the peta of solution was adjusted to 11-12 with 10 M NaOH. The mixture was filtrated and the resulting solid was washed with water and dried to obtain crude yellow solid product 110-4 (0.47 g, 65.8%). LCMS: m/z 428(M+1), 1H NMR(DMSO-J6) deltal.33 (m, 2eta), 1.54 (m, 4H), 2.32 (t, 2H), 2.42(s, 3H), 2.50(s, 3H), 3.20( t, 2H), 3.59 (s, 3H), 6.85 (m, 2H), 7.60 (t, IH), 7.69 (s, IH), 7.71 (m, IH), 10.88 (s, IH), 13.67 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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. 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

Preparation of ETHYL 2-(2-CHLOROBENZYLIDINE)-4-[2-(PHTHALIMIDE) ETHOXY] ACETOACETATE (XV : A 250 mL two-necked flask, equipped with a magnetic stirring bar and thermometer was charged with 10 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate and 3.96 g 2- chlorobenzaldehyde and 100 mL isopropanol under nitrogen atmosphere. To the resulting mixture was added 0.188 ML of acetic acid and 0.223 ML pyrolidine. The reaction mixture was heated to 37 C and stirred at this temperature for 5 hours. The solvent was removed in vacuo and the residue was dissolved in 100 ML of methylene chloride. The resulting solution was washed with 100 mL of sat. NAHCO3 and 100 mL of water, dried over 5 G OF MGS04. MGS04 was filtered off, the filtrate was concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexane (20/80) as an eluent to give 7.72 g of ethyl 2- (2-CHLOROBENZYLIDINE)-4- [2- (PHTHALIMIDE) ethoxy] acetoacetate as an light brown oil (yield 56%, rel. compound purity > 98%). 1H-NMR (CDCL3) No. 7.89 (s, 1H), 7.78 (dd, 2H), 7.69 (dd, 2H), 7.35 (M, 1H), 7.28 (M, 2H), 7.17 (M, 1H), 4.44 (s, 2H), 4.05 (Q, 2H), 3.76 (T, 2H), 3.64 (t, 2H), 1.20 (t, 3H). 13C-NMR (CDCI3) 6 203. 2,168. 4,164. 0,140. 0,134. 0,133. 9,132. 3,131. 5, 130.4, 129.8, 127.3, 126.8, 123.4, 77.7, 68.5, 62.0, 37.4, 14.3.

The synthetic route of 88150-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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. Product Details of 5181-35-1

To a solution of 2-(2- bromoethoxy)isoindoline- l,3-dione (5 g, 1.85 mmol, product from step 1 of preparation 10) and lH-tetrazole (1.3 g, 1.85 mmol) in dimethylformamide (25 ml) was added cesium carbonate (6.0 g, 1.85 mmol) in a lot wise under stirring at room temperature. The progress of reaction was monitored by performing thin layer chromatography using mixture of acetone and hexane (3.5:6.5) as solvent. After 16 hours the completion of the reaction was confirmed by thin layer chromatography. The reaction mixture was slowly poured into chilled water (200 ml) under stirring. After stirring for 30 minutes, the precipitates formed were filtered and washed with water (50 ml). The solid compound was dried at 40 C for 2 hours under high vacuum to provide 3.2 g of a mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2-(2H-tetrazol-2- yl)ethoxy]- lH-isoindole- l,3(2H)-dione in 66% yield. Analysis: Mass: 260 (M+l) for Molecular weight: 259 and for Molecular formula: C11H9N5O3; To a flask containing mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)- dione and 2-[2-(2H-tetrazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione (3.0 g, 1.15 mmol, product from step 1) in dichloromethane (30 ml) was added hydrazine hydrate (0.870 ml, 1.73 mmol) at 25-30 C under stirring and continued stirring for 2 hours. The progress of reaction was monitored by thin layer chromatography. After complete conversion, the unwanted solid was filtered out and washed with dichloromethane (12 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 1.5 g of crude mixture of l-[2-(aminooxy)ethyl]- lH-tetrazole and 2-[2-(aminooxy)ethyl]- 2H-tetrazole (about 100 % yield) and used without further purification in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5181-35-1, its application will become more common.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem