Author: Jessica.F

Electric Literature of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

Statistics shows that 2-(Bromomethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5332-26-3.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Recommanded Product: Isoindoline

To a stirred suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (0.53 g, 2.04 mmol, 1 eq.) and potassium carbonate (0.56 g, 4 mmol, 2 eq.) in N,N-dimethylformamide (5 mL) was added isoindoline (280 mu^, 2.45 mmol, 1.2 eq.). The resulting mixture was then stirred at room temperature for 17 hours. The solvent was removed in vacuo and the crude product was partitioned between water and dichloromethane, the layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography using a 10 – 100 % ethyl acetate in wo-hexane gradient to afford methyl 4- (isoindolin-2-ylmethyl)-3-methoxybenzoate as a red liquid (0.417 g, 70 % yield). NMR (400 MHz, CDC13) 7.66 (1H, d, J=7.8 Hz), 7.55-7.53 (2H, m), 7.18 (4H, s), 4.0-3.98 (6H, m), 3.92-3.91 (6H, m).

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; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1914-02-9, name is 3,3-Dimethylindoline, 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. COA of Formula: C10H13N

4a. 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline:; To 2a (90 mg, 0.61 mmol) was added 2-nitro-3-chloropyridine (200 mg, 1.26 mmol). The reaction mixture was heated at 220 C. microwave for 15 min. The desired compound was isolated via preparative HPLC to afford 4a (30 mg, 18%) as white lyophilizes. Column: Luna 25¡Á100 mm; Eluted from 35% CH3CN to 100% CH3CN in H2O with 0.1% TFA MS (ES) m/z 269 [M+H]+.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 41910-64-9 as follows. name: 4-Chloroindoline

To a mixture of 4-chloroindoline (3 g, 19.53 mmol) in H20 (3 mL) was added 2- hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixture was diluted with EtOAc. The organics were washed with H20, dried over Na2S04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (3.3 g). LCMS m/z = 192.8 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.02 (t, J = 8.2 Hz, 2H), 3.46 (t, J = 8.2 Hz, 2H), 4.28 (s, 2H), 6.60 (d, J = 2.1 Hz, 1H), 6.76 (d, J = 8.0Hz, 1H), 7.09 (t, J = 8.0 Hz, 1H).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
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

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

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

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

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

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