Category: indolines-derivatives

Related Products of 7477-63-6,Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, molecular formula is C8H4ClNO2, 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: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50°C for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 × 30 mL) and cold aqueous ethanol (2 × 1 mL) to afford pure product 4.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 isatin 1a (0.147 g, 1 mmol), malononitrile 2a (0.066 g, 1 mmol), and ethyl aceto-acetate 3a (0.13 mL, 1 mmol) was added to a vial containing a magnetic stirring bar and the ionic liquid ([BMIm]BF4, 5 drops). The reaction mixture was sealed and stirred at room temperature until disappearance of the starting materials (under 1 min). At this stage, the product due to poor solubility in the ionic liquid appears as a precipitate. In order to extract the ionic liquid, after completion of the reaction, the residue was washed with 2×10 mL of either water or diethyl ether. Washing the solid residue with ethanol (10 mL, 95.5%) has given remarkably pure powders of product 4a. The ionic liquid was recovered from the aqueous or ethereal extracts by evaporating under reduced pressure and reused in the next cycles.

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

Reference:
Article; Rad-Moghadam, Kurosh; Youseftabar-Miri, Leila; Tetrahedron; vol. 67; 31; (2011); p. 5693 – 5699;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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 mixture of indoline-5-carboxylic acid (500 mg, 3.07 mmol) in DMF (3 mL) was added Pyridine (0.2 mL) at 0 C followed by acryloyl chloride (555 mg, 6.13 mmol). The reaction mixture was stirred at RT for 5 h. The mixture was then concentrated, DCM was added (20 mL), washed with 0.5N HC1 (10 mL), dried over Na2504, filted and concentrated in vacuo to afford 1- acryloylindoline-5-carboxylic acid (280 mg, 42%) as a yellow solid. [M+H] Calc?d for C12H11N03:218.1; Found: 218.1

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-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 3416-57-7, name: 2-(2-Oxopropyl)isoindoline-1,3-dione

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

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, 2-(2-Oxopropyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. SDS of cas: 317-20-4

Potassium Hydroxide (1.58 g; 28.16 mmol; 3.1 eq.)was added portion wise to a solution of 7-Fluoro-1H-indole-2,3-dione(1.50 g; 9.08 mmol; 1.0 eq.) in acetone (1.0 mL; 13.63 mmol; 1.5 eq.), ethanol (4.50 mL) and water (1.50 mL) in a microwave tube. The reaction was placed in a microwave oven and heated at 100C for 20 min. The reaction mixture was concentrated under vacuum. Water was added followed by a 5N solution of hydrochloric acid until the pH of the solution reached 4. The suspension was then filtered and the solid obtained dried. 8-fluoro-2-methylquinoline-4-carboxylic acid (1.60 g; 85%) was isolated as a brown solid. MS(ES+) m/z 206 (MH+).

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

Reference:
Article; Boiteau, Jean-Guy; Ouvry, Gilles; Arlabosse, Jean-Marie; Astri, Stephanie; Beillard, Audrey; Bhurruth-Alcor, Yushma; Bonnary, Laetitia; Bouix-Peter, Claire; Bouquet, Karine; Bourotte, Marilyne; Cardinaud, Isabelle; Comino, Catherine; Deprez, Benoit; Duvert, Denis; Feret, Angelique; Hacini-Rachinel, Feriel; Harris, Craig S.; Luzy, Anne-Pascale; Mathieu, Arnaud; Millois, Corinne; Orsini, Nicolas; Pascau, Jonathan; Pinto, Artur; Piwnica, David; Polge, Gaelle; Reitz, Arnaud; Reverse, Kevin; Rodeville, Nicolas; Rossio, Patricia; Spiesse, Delphine; Tabet, Samuel; Taquet, Nathalie; Tomas, Loic; Vial, Emmanuel; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 945 – 956;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

B] Preparation of compound 1-B; 0.38 g (0.99 mmol) of compound 1-A is dissolved in 15 ml methanol and 0.26 g (1.28 mmol) of 3-(l,3-dioxo-l,3-dihydroisoindol-2-yl)-propionaldehyde, 0.1 ml acetic acid and 0.125 g (1.98 mmol) OfNaBH3CN are added to the solution. The mixture is stirred at 28C for 3.5 hours and the solvent is subsequently evaporated. The crude product is purified by column chromatography on silica gel (petroleum ether(ethyl acetate 10:1 -> 5:1) to give 380 mg (65%) of the desired product as a light yellow solid.

The synthetic route of 3-(1,3-Dioxoisoindolin-2-yl)propanal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; KELLENBERGER, Johannes, Laurenz; DREIER, Juerg; WO2011/18510; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

Under argon atmosphere, 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) was dissolved in tetrahydrofuran(5mL). A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6): delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chlorooxindole, its application will become more common.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1514544; (2005); A1;,
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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, A new synthetic method of this compound is introduced below., Formula: C13H14BrNO2

General procedure: A suspension of isovanillin (8 g, 52.6 mmol, 1 equiv), anhydrous K2CO3 (10.9 g, 78.9 mmol, 1.5 equiv), and KI (1.75 g, 0.1 equiv) in dry DMF (50 mL) was stirred and heated to 65C. Compounds 6a-d (68.4 mmol, 1.3 equiv) was added portionwise over 1 h and the stirred mixture heated at 65 C for a further 18 h. After cooling to room temperature, the reaction mixture was treated with 1M aqueous HCl (100 ml), and extracted with CCl3H (2 × 100 ml), The combined organic extracts were separated, dried, filtered, and concentrated. The residue was purified by flash chromatography to provide 7a-d as a white solid. Isovanillin was treated with compound 6c according to general procedure to give the desired product 7c as a white solid, yield 81%.

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; Liu, Anqiu; Huang, Ling; Wang, Zhiren; Luo, Zonghua; Mao, Fei; Shan, Wenjun; Xie, Jiaxing; Lai, Kefang; Li, Xingshu; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1548 – 1552;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20870-90-0, The chemical industry reduces the impact on the environment during synthesis 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of the corresponding oxindole (1.0 equiv) in EtOH (0.7 M) at room temperature was added sequentially 2-bromobenzaldehyde (1.2 equiv) and piperidine (0.1 equiv). The reaction mixture was heated to reflux and stirred until the starting oxindole was consumed as judged by TLC (ca. ~4 h). The reaction was allowed to cool to room temperature by removal of the oil bath, and then concentrated under reduced pressure. The crude mixture was purified by flash chromatography eluting with hexanes/EtOAc at the indicated ratio to afford the title compound.

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-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wilson, Erin E.; Rodriguez, Kevin X.; Ashfeld, Brandon L.; Tetrahedron; vol. 71; 35; (2015); p. 5765 – 5775;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem