Category: indolines-derivatives

Application of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-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.

To a 5 L 4-neck flask (equipped with a mechanical stirrer, condenser, N2 inlet and NAOH scrubbing solution) was charged sequentially with carbon disulfide (CS2) (1.5 L), anhydrous aluminum chloride (AIC13) (2.7 mol, 359 g, 6 equiv) and CHLOROACETYL chloride (0.585 mol, 66.1 g (46.6 mL), 1.3 equiv). 1- methyl-1, 3-dihydroindol-2-one (0.45 mol, 66.2 g, 1 equiv) was added portionwise over 1 hour; the addition was accompanied with temperature increase of 20–> 310 C. After the addition of 1-methyl-1, 3-dihydroindol-2-one was complete the reaction mixture was stirred 0.75 hour at which time stirring of the reaction mixture was not possible. The reaction mixture was refluxed for 3.5 hours then cooled to room temperature. The carbon disulfide (CS2) was decanted, the residue cooled in an ice/water bath. The reaction mixture was quenched by very slow addition of ice and water. The resulting tan suspension was stirred overnight at room temperature. The solids was collected, washed with water (4X), dried on the filter for 15 min followed by drying overnight in hood. The product was further dried in a vacuum oven at- 50 C for 24 hours; the product was pulverized and dried in a vacuum oven for an additional 3 hours AT-70 C to give 91.6 g (91%) of 5-(2-CHLOROACETYL)-1- METHYL-1, 3-dihydroindol-2-one of a salmon colored solid, mp 197-200 C.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/37820; (2004); A1;,
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Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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: A mixture of 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (1 g, 4 mmol) [Maybridge, cat10430564], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (1.7 g, 6.6 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.2 mmol) and potassium acetate (1.3 g, 13 mmol) in 1,4-dioxane (40 mL) was purged with nitrogen and then stirred at 90 C. overnight. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.1. found 274.1.

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; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
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Application of 1504-06-9, A common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4BrNO2

Compound E-1 (110 mmmol) was refluxed in formamide for 4 hours to obtain compound E-2 (103 mmol, 94%).Compound E-2 (100 mmol) was reacted in 28% ammonia solution at room temperature for 24 hours to obtain compound E-3 (74 mmol, 74%).Compound E-3 (70 mmol) was dissolved in DMF,The mixture was allowed to react with thionyl chloride in an ice bath for 24 hours to obtain compound E-4 (53 mmol, 75%).

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 6941-75-9.

Reference:
Patent; NIPPON STEEL & SUMIKIN CHEMICAL COMPANY LIMITED; KYUSHU INSTITUTE OF TECHNOLOGY; HAYASE, SHUZI; PANDEY, SHYAM SUDHIR; YAMAGUCHI, YOSHIHIRO; OCHI, NORIAKI; FUJINO, KENICHI; OKAMOTO, ETSUYA; KOMAYA, YOHEI; (25 pag.)JP5906522; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 919103-45-0, name is 6-Iodoindolin-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 919103-45-0, Recommanded Product: 919103-45-0

0.88 g (7.23 mmol) 4-/V,/V-dimethylaminopyridine and 44.6 mL (101 .2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1 ,3-dihydro-indol-2- one in 125.0 mL /V,/V-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10C to the reaction mixture and stirred for 2 h at -10C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL cone, hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50C in vacuo. [M+H]+: 364

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; BISTER, Bojan; SINI, Patrizia; WO2014/9319; (2014); A1;,
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Application of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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Reference of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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 6 4-(4-Chloro-2,3-dihydro-indol-1-yl)-6,7-dimethoxy-quinazoline Utilizing a procedure analogous to that described in Example 2, this product was prepared in 92% yield from 4-chloro-indoline (2 eq.) and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 172-179 C. (dec); LC-MS: 342 (MH+); anal. RP18-HPLC RT: 4.60 min.).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
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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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., SDS of cas: 19727-83-4

6-Aminoindoline A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 H NMR (400 MHz, CDCl3) 7.40 (d,J=7.4, 1H), 6.05 (d,J=2.0, 1H), 6.03 (d,J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t,J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t,J=8.2, 2H).

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; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 1127-59-9, name is 7-Methylindoline-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 1127-59-9, Formula: C9H7NO2

General procedure: Compound B (11.9 mg, 0.02 mmol) was added at 4 C in a mixed solution of Eosin 1a (29.4 mg, 0.2 mmol) and methyl acetoacetate 2a (107.8 muL, 1.0 mmol) in tetrahydrofuran (1.0 mL). The reaction was stirred at 4 C for 96 hours. Spin-drying, column chromatography (petrole ether: ethyl acetate = 1 : 1-1 : 2), and evaporated to give a pale yellow amorphous solid 49.0mg, yield 93%, 90% ee.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui University of Technology; Zhang Dongxin; Yin Lei; Zhong Junchao; Man Jingjing; Chen Yan; Zhang Qianfeng; (21 pag.)CN110041243; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Application In Synthesis of 2-Oxoindoline-5-carboxylic Acid

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.

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