Category: indolines-derivatives

Reference of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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 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-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5j): Melting point 295-297 C; White solid, 92%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.69-4.72 (m, 1H), 4.41 (d, J = 10.24 Hz, 1H), 3.87 (d, J = 13.92 Hz, 1H), 3.83 (s, 3H), 3.81 (s, 3H), 3.72 (d, J = 16.92 Hz, 1H), 3.55 (d, J = 15.4 Hz, 1H), 3.05 (d, J = 11.72 Hz, 1H), 2.84-2.90 (dd, J = 13.96, 8.08 Hz, 1H), 2.75 (d, J = 13.92 Hz, 1H), 6.62-6.68(m, 2H), 6.99-7.58 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.7, 47.4, 52.7, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.9, 109.8, 114.1, 114.3, 121.3, 122.4, 124.6, 124.9, 126.5, 127.4, 128.6, 128.7, 128.6, 128.7, 129.4, 129.8, 130.2, 130.5, 131.7, 134.5, 136.8, 138.4, 138.5, 138.7, 139.8, 139.9, 140.2, 144.4, 179.3, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.69; H,5.36; N, 5.58.

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H15BrFNO2

1.1-dimethylethyl 4-fluoro-5-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)-2.3-dihydro-1H-indole-1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)*CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-dioxane (20 ml_) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 : 1 saturated aqueous NaCI: H20 (100 ml_) and ethyl acetate (100 ml_), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes, 40 g silica gel column) to afford 1 , 1- dimethylethyl 4-fluoro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H- indole- 1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1.51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 – 7.61 (m, 2 H).

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 1337533-31-9.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
Indoline – Wikipedia,
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These common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, 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. Recommanded Product: 18711-15-4

3) Intermediate I-3; 2-amino-4,6-dichloro benzoic acid; At room temperature, to a solution of the intermediate I-2 (5.0 g, 23.1 mmol) prepared by the above peparation example I(2) in 75 mL 1N NaOH (aq) was added portionwise hydrogen peroxide (28 % v/v, 10 mL). The reaction mixture was filtered after stirring for 2 hours to remove insoluble dark brown solid. The filterate was then carefully acidified to pH 2 by conc. hydrochloric acid. The formed yellow precipitates were collected, washed with water, and dried in vacuo. The objective compound (3.90 g, 82 %) was obtained as ivory-colored solid by recrystalization from benzene: TLC Rf = 0.1 (EtOAc:n-hexane = 1:1); m.p. 188 – 189 C; 1H NMR (DMSO-d6) delta 6.76 (d, J = 1. 9 Hz, 1H, ArH), 6.85 (d, J = 1. 9 Hz, 1H, ArH); MS(EI) m/e 206[M+], 162[M+-CO2].

The synthetic route of 4,6-Dichloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; EP1650190; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 147149-84-6,Some common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-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: To a microwave reaction tube were added indoles (2 mmol), isatins (1 mmol) and HFIP (2 mL). After sealing the tube, the mixture was heated to 75C in an oil bath and stirred for 1 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, and the resulting precipitate was then filtered, washed with ether, and dried to give compound 3a-3q and 4a-4j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-5-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Cheng, Jialing; Liu, Hong-Min; Wang, Shuai; Yu, Bin; Yuan, Xiaohan; Chinese Chemical Letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, Computed Properties of C8H4ClNO2

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.

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; Safaei-Ghomi, Javad; Nazemzadeh, Seyed Hadi; Shahbazi-Alavi, Hossein; Catalysis Communications; vol. 86; (2016); p. 14 – 18;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64483-69-8, name is 5-Acetylindolin-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 64483-69-8, Recommanded Product: 64483-69-8

The 5-acetyloxindole (54 g, 308 mmol), acetic acid (400 ml) and palladium on carbon (10%, 5 g) are combined and treated with hydrogen for 14 hours at 55 psi. The catalyst is removed by filtering through a bed of Celite, the filtrate is concentrated under reduced pressure and the residue is treated with ether to give 5-ethyloxindole

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

Reference:
Patent; Novartis AG; US6291523; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 356068-93-4,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.

EXAMPLE 9: Preparation of (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)- TV- (7-(hydroxyl-amino)-7-oxoheptyl)-2,4-dimethyl-lH-pyrrole- 3-carboxamide (Compound 15) Step 9a. (Z)-Methyl 7-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl- lH-pyrrole-3-carboxamido)heptanoate (Compound 110-15)To a stirred solution of compound 109 (220.0 mg, 0.73 mmol) in DMF (15 mL) at room temperature was added etaOBt (148.6 mg, 1.1 mmol), triethylamine(0.21 mL, 1.46 mmol), ECDI-etaC1 (210.2 mg, 1.1 mmol) and methyl 7- aminoheptanoate hydrochloride (157.1 mg, 0.8 mmol) successively. The mixture was stirred for 24 h at room temperature and was then diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL). The peta of the mixture was adjusted to 11-12 with 10 N NaOH. The mixture was filtered and the solid was washed with water, dried to obtain a crude product 110-15 as a yellow solid (0.3 g, 93.2%). LCMS: 442 [M+lf; 1H NMR(DMSO-^6): delta 1.31 (m, 4H), 1.50 (m, 4H), 2.31 (t, J= 7.35 Hz, 2H), 2.40 ( s, 3H), 2.42 (s,3H), 3.19 (m, 2H), 3.59 (s, 3H), 6.87 (m, 2H), 7.71 (m,3H), 10.91 (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 (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 222036-66-0, 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. 222036-66-0, name is 5-Aminoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 5-((5-oxo-2,5-dihydro-1H-pyrrol-3-yl)amino)isoindolin-1-one (Cpd. No. 9) A mixture of pyrrolidine-2,4-dione (1, 18 mg, 0.18 mmol) and 5-aminoisoindolin-1-one (2, 27 mg, 0.18 mmol) in methanol (1 mL) was stirred at 60¡ã C. for 1 h. Upon cooling, the mixture was filtered, followed by rinsing with methanol. The solid was dried under vacuum to afford 5-((5-oxo-2,5-dihydro-1H-pyrrol-3-yl)amino)isoindolin-1-one (Cpd. No. 9) as an off-white solid. Yield: 23 mg, 55percent; 1H NMR (300 MHz, DMSO-d6) delta 9.44 (s, 1H), 8.28 (s, 1H), 7.57 (d, J=4.8 Hz, 1H), 7.32 (s, 1H), 7.19 (s, 1H), 7.15 (dd, J=1.2, 5.1 Hz, 1H), 5.40 (s, 1H), 4.32 (s, 2H), 4.01 (s, 2H).

The synthetic route of 5-Aminoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 193354-13-1, 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. 193354-13-1, name is 5-Iodoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

The chemical industry reduces the impact on the environment during synthesis 5-Iodoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

3-lodo-4-methylbenzoic acid (262 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. Of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction were stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1 N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 301 mg (83%) of the product as a tan solid. MS (+ESI): m/z 363.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Isoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem