Category: indolines-derivatives

Related Products of 18711-13-2, These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-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.

3-(2-(4-(Azetidin-l-yl)phenyl)-2-oxoethyl)-4,7-dichloro-3-hydroxyindolin-2-one (E To 4,7-dichloroindoline-2,3-dione (A) (300 mg, 1.39 mmol) in 15 niL of methanol were added l-(4-(azetidin-l-yl)phenyl)ethan-l-one (B) (972 mg, 5.5 mmol) and a few drops of diethylamine (2). The reaction was stirred at rt for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CH2C12) to get an off white solid. 3-(2-(4-(Azetidin-l-yl)phenyl)-2-oxoethyl)-4,7-dichloro-3-hydroxyindolin-2-one (EXAMPLE 13): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 2.32 (m, 2H), 3.51 (d, 1H, J=16 Hz), 3.95(m, 4H), 4.30 (d, 1H, J=16Hz), 6.35(s, 1H), 6.36 (d, 2H, J=8Hz), 6.87 (d, 1H, J=8Hz), 7.28 (d, 1H, J=8Hz), 7.73 (d, 2H, J=8Hz), 10.89 (s, 1H).

Statistics shows that 4,7-Dichloroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 18711-13-2.

Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
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Application of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 37a; Preparation of intermediate E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester; To a mixture of 6-chlorooxindole (4.58 g, 20 mmol) and 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10 g, 26 mmol) in methanol (50 mL) was added piperidine (2.56 mL, 26 mmol) dropwise. The mixture was then heated at 100 C. for 3 h. After cooled to 4 C., the mixture was filtered and the precipitate was collected, dried to give the title compound as a bright yellow solid (12.4 g, 90%).

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

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H4F3NO3

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
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Related Products of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

ally:3L reaction flask was added dichloromethane 800mL, Et2NH (175.5mL, 1.68mol, 2.1eq), K2CO3 (121.6g, 0.88mol, 1.1eq), a mechanical stirrer, nitrogen atmosphere, was cooled to 0 deg.] C, was added dropwise over 25 minutes 3- [2- (1,3-diketo isoindoline)] propanal (162.55g, 0.80mol, 1.0eq) dissolved in 800mL DCM solution was added dropwise to 0 stirred for 5 minutes, then at room temperature for 3 hours.After concentrating the solvent was filtered off portion, the filtrate was concentrated dryness to give 199.93g crude D2, crude yield: 97%.(Instability resulting intermediate, required stored at -20 ).

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jie Da Wei (Shanghai) Pharmaceutical Technology Development Co., Ltd; Tang, Yanlin; Chen, Keshi; (10 pag.)CN105906569; (2016); A;,
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Electric Literature of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

Example 13; Synthesis of 4-chloro-6-(1.3-dihvdro-2H-isoindol-2-yl)pyrimidin-2- amine (Intermediate 18); 4,6-Dichloropyrimidin-2-amine (1.12g), isoindoline (1.2ml), and triethylamine (1.63ml) in EtOH (33ml) are heated with stirring at 85 0C for 6 hours. The solvent is removed in vacuo, and the residual solid suspended in DCM (40ml) and dilute citric acid solution (30ml). The suspended solid is filtered off, washed with DCM and water, and dried to afford the title compound as a grey solid (1.573g, 93%). LCMS 247 [M+H]+, RT 3.05 mins (pH 2.5). 1H NMR 300 MHz (CDCI3) (delta ppm): 7.25 – 7.48 (4H, m), 6.58 (2H, s), 5.92(1H, s), 4.71 (4H, br d).

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA, S.A.; WO2008/31556; (2008); A2;,
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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 169037-23-4 as follows. HPLC of Formula: C9H4F3NO3

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o-chlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-chlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5d): Melting point 276-278 C White solid, 93%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.91 (d, J = 14.00 Hz, 1H), 4.61-4.68 (m, 1H), 4.20-4.27 (m, 1H), 3.87 (d, J = 13.2 Hz, 1H), 3.62 (d, J = 16.82 Hz, 1H), 3.35 (d, J = 15.4 Hz, 1H), 2.98 (d, J = 13.96 Hz, 1H), 2.77-2.84 (m, 1H), 2.45 (d, J = 13.92 Hz, 1H), 6.52-6.61 (m, 2H), 6.89-7.54 (m, 21H, Ar); 13C-NMR(CDCl3, 100 MHz): delta/ppm 40.5, 47.3, 51.9, 53.2, 62.9, 65.7, 73.2, 98.8, 110.1, 120.4, 122.5, 123.9, 124.1, 126.4, 126.5, 127.0, 128.0, 128.1, 128.2, 128.3, 128.4, 128.6, 128.9, 129.1, 129.7, 129.8, 130.5, 132.4, 132.9, 135.5, 136.3, 137.7, 138.8, 139.9, 144.4, 179.7, 198.9. EI-MS: m/z 780 (M+). Anal. Calcd for C44H34Cl2F3N3O3: C, 67.70; H, 4.39; N, 5.38; Found: C, 67.57; H, 4.47; N, 5.28.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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Related Products of 7147-90-2, 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 7147-90-2 as follows.

2-chloro-6-bromoquinoline (240 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol)5-chlorophthalimide (360 mg, 2 mmol), sodium carbonate (210 mg, 2 mmol),Acetonitrile (2 ml) was added to the dry reaction tube and suspended in an oil bath at 120 C for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 378 mg of colorless solid2- (2- (4- (6-bromoquinolyl) 2-piperazinyl) 1-ethyl) -5-chloroisoindole-1,3-dione,The yield was 76%.

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
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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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3484-35-3

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
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Electric Literature of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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: To mixture of isatins (1 mmol), malononitrile (1 mmol), and dimedone or 4-hydroxycoumarin or barbituric acids (1 mmol) in ethanol (4 mL), 5mg of Fe3O4APTPOSS MNPs added as the catalyst, and the mixture was stirred for an appropriate time at room temperature (Table 2). The reaction was monitored by TLC. After completion of the reaction, precipitate was filtered and dried in a drying oven to furnish 2-aminopyrano-3-carbonitriles.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Safaei-Ghomi, Javad; Nazemzadeh, Seyed Hadi; Shahbazi-Alavi, Hossein; Catalysis Communications; vol. 86; (2016); p. 14 – 18;,
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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. 435273-55-5, name is 4-Bromo-2-methylisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 435273-55-5

Compound 1 L: 4-Bromo-2-methyl-7-nitro-2,3-dihydro-1 H-isoindol-1 -oneAn 8M solution of methylamine in ethanol (10 mL, 80 mmol) was added to a solution of methyl 3-Bromo-2-(bromomethyl)benzoate in THF (30 mL) and allowed to stir for 2h. The reaction mixture was concentrated to dryness and the residue was triturated with water. The solids produced were collected by filtration and dried to afford 4-bromo-2-methyl-2,3- dihydroisoindol-1-one which used immediately in the next step. To a cold suspension of 4- bromo-2-methyl-2,3-dihydroisoindol-1 -one (60 g, 265 mmol) in concentrated sulfuric acid (60 mL) was added pre-cooled mixture of cone, nitric acid (12.5 mL, 265 mmol) and cone, sulfuric acid (60 mL) over 20 min. The reaction mixture was stirred for 30 min at 0 C and 2h at room temperature. The reaction mixture was poured into an ice-water mixture (300 mL) and the precipitate that formed was collected by filtration and washed with water (3×100 mL). The solids were suspended in isopropanol (200 mL) and heated on a steam bath for 10 minutes. The mixture was cooled and the solid was collected by filtration and air dried to afford 53 g of the title compound (74 %). 1H NMR (CDCI3, 300 MHz) delta 3.22 (s, 3H), 4.36 (s, 2H), 7.67 (d, J = 8.4= 8.4 Hz, 1 H).

The synthetic route of 435273-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
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