Author: Jessica.F

Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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. Recommanded Product: 356068-93-4

EXAMPLE 4: Preparation of 7V-(5-(hvdroxycarbamoyl)pentyl)5-((Z)-(5-fluoro- 2- oxoindolin-3-ylidene)methyl)-2,4-dimethyl-lH-pyrrole-3- carboxamide (compound 4) Step 4a. Methyl 6-(5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl) -2,4- dimethyl- lH-pyrrole-3-carboxamido)hexanoate(compound 110-4) To a stirred solution of compound 1 (0.5 g, 1.67 mmol) in DMF (35 mL) 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^.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-^6) deltal.33 (m, 2H), 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).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 356068-93-4, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
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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. 39755-95-8, name is 5-Methoxyisatin, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxyisatin

A mixture of 5-methoxyisatin (2.84 g, 16 mmol) and K2CO3 (5.53 g, 40mmol) was dissolved in anhydrous DMF (12 mL) under Ar. Benzylbromide (5.71 mL, 48 mmol) was added dropwise and the mixturewas stirred at r.t. for 19 h. The mixture was extracted with dichloromethane (3 × 20 mL) and the organic phase was washed with H2O (20mL) and brine (20 mL), dried with MgSO4, filtered, and concentratedto obtain a red solid.14The crude material was dissolved in DMSO (12mL), hydrazine hydrate (1.81 mL, 32 mmol) was added dropwise andthe mixture was heated at 150 C for 5 h. The mixture was cooled tor.t., extracted with EtOAc (2 × 100 mL), and the organic phase waswashed with H2O (100 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (hexane/EtOAc) to give pure 1-benzyl-5-methoxy-2-oxindole (2.55 g, 63%) as a brown oil.15The above product was dissolved in acetic anhydride (11.5 mL, 121mmol) and DMAP (37 mg, 0.3 mmol) was added. The mixture was heated at reflux (140 C) for 6 h and then cooled to r.t. and evaporated under reduced pressure. The residue was dissolved in MeOH (40 mL)cooled at 0 C and then a solution of KOH (8.5 g, 151 mmol) in MeOH (60 mL) was added. The solution was stirred at r.t. for 18 h then the solution was cooled in an ice-bath at 0 C and 12 M aqueous HCl was added until pH 3. The organic solvent was evaporated under reduced pressure, H2O (50 mL) was added and the mixture was extracted with EtOAc (3 × 50 mL). The organic phase was dried over MgSO4, filtered,and concentrated. The residue was purified by flash chromatography(hexane/EtOAc) to give pure 2c.

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; Ortega-Martinez, Aitor; Molina, Cynthia; Moreno-Cabrerizo, Cristina; Sansano, Jose M.; Najera, Carmen; Synthesis; vol. 49; 23; (2017); p. 5203 – 5210;,
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Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-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 60434-13-1, Computed Properties of C9H6ClNO2

General procedure: A solution of N-methylisatin (161 mg, 1.0 mmol), N-methylindole (262 mg, 2.0 mmol), and p-TsOH . H 2 O (19 mg, 0.1 mmol) in CH 2 Cl 2 (2.0 mL) was stirred at room temperature for 1 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 2:1), 1a was obtained as a white solid, 301 mg (74%). 1 Other compounds 1b-f, 1i, 1j, and 1n were synthesized similarly, and compounds 1a1 and 1n1 are known compounds. The spectroscopic data of unknown compounds 1b-f, 1i, and 1j are as follows.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Seo, Da Young; Kim, Gieun; Jo, Hwi Yul; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 4; (2018); p. 587 – 590;,
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Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-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 118289-55-7, Quality Control of 6-Chloro-5-(2-chloroethyl)indolin-2-one

8. Preparation of ZPR in glycerol by Na C03 portion-wise addition To a three necked flask was charged BITP HC1 (15g), CEI (16. 2g), glycerol (60ml) and Na2C03 (3. 11 g, 0. 5mol). The reaction mixture was heated at 115 C and after 15′ a new portion of 0.12 mol Na2C03 was added. The heating was continued by addition of 0.12 mol base each hour. After 5 hours the base addition was completed and the reaction mixture was heated for an additional hour. After cooling to room temperature, the mixture was diluted with water (120ml) and after 1 hour stirring the product crude was filtrated, washed with water and dried at 50C to afford 25.7g dried product (yield 82. 4%) (purity by HPLC 94%).

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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
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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. 61-70-1, name is 1-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Methylindolin-2-one

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

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 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

General procedure: A mixture of isatoic anhydride 1 (1 mmol), isatin 2 (1 mmol), phenyl hydrazine 3 (1 mmol), 0.3 g (0.6 mmol) alum, and 10 ml EtOH in a 50 ml flask was stirred at reflux for time period asindicated in Table 1. After completion of the reaction (monitored by TLC, ethylacetate/n-hexane,1:1), 25 ml EtOH was added to the reaction mixture, and recrystallized from ethanol to afford pure product.

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Article; Mohammadi, Ali A.; Askari, Saber; Rohi, Hamed; Soorki, Ali Abolhasani; Synthetic Communications; vol. 44; 4; (2014); p. 457 – 467;,
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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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., Formula: C10H13N

A mixture of 3,3-dimethylindoline (5s, 103 mg, 0.700 mmol), potassium carbonate (288 mg,2.084 mmol), and 2-bromopropanenitrile (303 muL, 3.506 mmol) in 2 mL CH3CN was stirred at 80C overnight. The mixture was concentrated and purified by preparative HPLC. Fractions containing productwere partly concentrated and residue was extracted with 1 M NaHCO3 and CH2Cl2. Organic phases weredried over MgSO4, filtered, and concentrated to give 2-(3,3-dimethylindolin-1-yl)propanenitrile (105mg). LCMS m/z = 201.2 [M+1]+; 1H NMR (400 MHz, CDCl3) delta ppm 1.26 (s, 3H), 1.40 (s, 3H), 1.63 (d, J = 7.3Hz, 3H), 3.05 (d, 1H, J = 8.2 Hz), 3.25 (d, 1H, J = 8.2 Hz), 4.57 (q, 1 H, J = 7.3 Hz), 6.57 (d, 1H, J = 7.9 Hz),6.83-6.87 (m, 1H), 7.06 (dd, 1H, J1 =7.4 Hz, J2 = 0.8 Hz), 7.12-7.16 (m, 1H).

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; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
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Application of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An equivalent mixture of aldehyde (1 mmol) and active methylene compound- barbituric acid/1, 3-dimethyl barbituric acid/ 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1 mmol) in dimethyl formamide (2 mL) was subjected to microwave irradiations at 150 C for 1 h. The reaction was monitored by TLC. After the completion, the reaction was quenched by adding water to the reaction mixture. The crude product was separated out as solid, which was further purified by washing with ethanol, hot water and recrystallization from chloroform:methanol (9:1).

The synthetic route of 1-(2,6-Dichlorophenyl)-2-indolinone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Harpreet; Kaur, Manpreet; Kaur, Harpreet; Sharma, Indu; Bhandari, Anmol; Kaur, Gurcharan; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
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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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 39603-24-2

General procedure: A mixture of isatin (1 mmol), thiosemicarbazide/4-methyl-3-thiosemicarbazide (1 mmol) was taken in 5 cm3 watercontaining 20 mol% of [2-HMPyBSA]HSO4 and stirred atroom temperature for the time specified in Table 2. Theprogress of reaction was monitored by TLC. After completionof the reaction, the reaction mixture was filteredand washed with ethanol to yield corresponding product inpure form. Products were characterized by usual spectraltechniques. (i.e. IR, 1H, 13C NMR, and MS).

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; Korade, Suyog N.; Patil, Jayavant D.; Pore, Dattaprasad M.; Monatshefte fur Chemie; vol. 147; 12; (2016); p. 2143 – 2149;,
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Application of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL×2) to afford the pure products as solid powder in good to excellent yields without further purification.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
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