Category: indolines-derivatives

Electric Literature of 675109-26-9, 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. 675109-26-9, name is 6-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

[0420] To a solution of Example 59a (317 mg, 1.5 mmol), Example 59b (470 mg, 1.5 mmol), K3P04 (636 mg, 3 mmol), Cul (29 mg, 0.15 mmol) in dioxane (7 mL) was added N1,N2-dimethylcyclohexane- 1,2-diamine (43 mg, 0.3 mmol). Then mixture was degassed with N2 three times and sealed, which was stirred at 100C for 30 min under microwave. The mixture was diluted with water (100 mL) and extracted with DCM (100 mL*l, 50 mL*2) The combined DCM layer was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH = 100/0 to 94/6) to give the desired productExample 59c (400 mg, yield 67%) as a pale yellow solid. LCMS [M+l]+ = 397.9

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, SDS of cas: 118289-55-7

Sodium carbonate (56.3 g) and 500 mL of water were placed into a round bottom flask. Added was 50 g OF 3- (1-PIPERAZINYL)-1, 2-BENZISOTHIAZOLE hydrochloride and 50 g of 6-CHLORO-5- (2-CHLOROETHYL) OXINDOLE. The reaction mixture was then refluxed for 15 hours. The reaction completion was monitored by TLC. The reaction mass was cooled to room temperature. The resulting compound was filtered and washed with 50 mL of water. The wet compound and 250 mL of acetone were placed into a flask and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to give a solid cake, which was washed with 50 mL of acetone. The wet cake and 750 mL of methanol were placed into a flask, which was heated to 50C, and 14 mL of methane sulfonic acid was added to the solution over 20 minutes. The resulting reaction mass was cooled to room temperature and was subjected to a filtration to give a solid compound, which was washed with methanol. The wet compound and 750 mL of water were placed into a flask, and then pH of the solution was adjusted to pH 9 with caustic lye. The reaction mixture was then stirred at room temperature for 1 hour and filtered. The filtered compound was washed with water and dried at 70C to give 65 g of crystalline form Ziprasidone base.

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; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES INC.; WO2004/50655; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

A solution of 4-formylbenzene sulfonyl chloride (1) (0.50 g, 2.44 mmol) in dichloromethane (5 mL) was treated with isoindoline (0.32 g, 2.68 mmol) and triethylamine (0.41 mL, 2.93 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The crude material (0.67 g, 96% yield) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.06 (s, IH), 8.05-8.00 (m, 4H), 7.25-7.20 (m, 2H), 7.20-7.14 (m, 2H), 4.66 (s, 4H); ESI+ MS: m/z (rel intensity) 288.0 (100, [M+H]+).

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METASTATIX, INC.; WO2008/109154; (2008); 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. 21857-45-4, name is 5-Methoxyindoline, A new synthetic method of this compound is introduced below., Safety of 5-Methoxyindoline

Part B 5-Methoxyindoline and di-tert-butyl dicarbonate (8.95 g, 1.2 eq.) were stirred in THF overnight at room temperature. The solution was concentrated in vacuo and recrystallized from Et2O/hexane to give 1-(tert-Butoxycarbonyl)-5-methoxyindoline (6.25 g, 74% yield for two steps).

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; DuPont Pharmaceuticals Company; US6245769; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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. Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

(S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate To a mixture of No. 5447725 (Compound G; 40 mg, 0.07 mmol), DBU (26 muL, 0.171 mmol), and dichloromethane (0.57 mL) was added 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) commercially available from Aldrich (cat. No. 252611-5G). After the mixture was stirred at room temperature for 17 hours, further 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) and DBU (9 muL, 0.057 mmol) were added. After further 2 hours, the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl) 1-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (51 mg, 89%; ESI (LC/MS positive mode) m/z 1018 (M+H); Rt 3.40 min.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-26-3, its application will become more common.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Safety of 5-Nitroindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A. Synthesis of 4-bromo-1-(pyridin-2-ylmethyl)-1H-indole-2,3-dione To a solution of 4-bromoisatin (8.94 g, 39.5 mmol) in anhydrous N,N-dimethylformamide (100 mL) was added sodium hydride (3.34 g, 86.9 mmol, 60percent dispersion in mineral oil) in portions at 0¡ã C. The brown reaction mixture was stirred for 30 min followed by the addition of a solution of 2-(bromomethyl)pyridine hydrobromide (10.0 g, 39.5 mmol) neutralized with sodium hydride (1.52 g, 39.5 mmol, 60percent dispersion in mineral oil) in N,N-dimethylformamide at 0¡ã C. The reaction mixture was stirred for 16 h and quenched with water (100 mL). The reaction mixture was extracted with diethyl ether (3*100 mL) and the aqueous layer was extracted with ethyl acetate (3*100 mL). The combined organic layers was washed with water (5*200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether to afford the title compound (10.6 g, 85percent) as a brown solid: 1H NMR (300 MHz, DMSO-d6) delta 8.53 (d, 1H), 7.67 (t, 1H), 7.30 (t, 2H), 7.25-7.19 (m, 2H), 6.94 (d, 1H), 5.04 (s, 2H); 13C NMR (75 MHz, DMSO-d6) delta 180.5, 157.3, 154.2, 152.3, 149.5, 138.4, 137.5, 128.6, 123.3, 122.3, 121.5, 116.4, 110.3, 45.8.

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

Reference:
Patent; XENON PHARMACEUTICALS INC.; US2010/173967; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. name: 1-Acetylindolin-3-one

Butyl -2 -acetylenic acid 4 – nitrophenyl-unit (61.5 mg 0.3 mmol), was used. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 3h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 24 mg and gave rise 68% to unit_.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: indolines-derivatives

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 305 mg (1.88 mM) of 4-Aminophthalimide in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100C, then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80C to yield 348 mg of 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp = 248-251C.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth Holdings Corporation; EP1117659; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 552330-86-6

Step A: 5-Bromo-1-oxo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester To a solution of 5-bromo-2,3-dihydro-isoindol-1-one (10.0 g, 47.4 mmol) in THF (100 mL) was added a solution of (Boc)2O (20.6 g, 94.5 mmol), and DMAP (0.57 g, 4.6 mmol). The reaction mixture was stirred at ambient temp overnight. Upon completion, the reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography (EA:PE=1:10) to afford the title compound (13 g, 88%).

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Chen, Young K.; Wallace, Michael Brennan; (110 pag.)US2017/183325; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem