Author: Jessica.F

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 60434-13-1 as follows. Product Details of 60434-13-1

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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, SDS of cas: 32692-19-6

Reference Example 98To 5-nitroindoline (1.Og, 6. lmmol) in acetone (12ml), powdered potassium hydroxide (1.7g, 30.5mmol, 5eq) was added followed by the addition of methyl iodide (1.2g, 9. lmmol, 1.5eq) at 00C. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and water was added and the compound was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to yield l-methyl-5 -nitro-2,3-dihydro-l H-indole (l.Og, 92%). The crude compound was used in the next stage without purification. Reference Example 103 l-Methyl-2,3-dihydro-lH-indol-5-ylamine a) Preparation of l-methyl-5-nitro-2,3-dihydro-lH-indoleTo a solution of 5-nitro-2,3-dihydro-lH-indole (Ig, 6.09mmol) in acetone (12ml) was added powdered potassium hydroxide (1.7g, 30.45mmol), followed by methyl iodide (1.2g, 9.14mmol) and stirred overnight at ambient temperature. The solvent was evaporated under vacuum to give a residue, to which water was added and the product extracted with ethyl acetate. Drying and concentration of the organic layer yielded 1- methyl-5-nitro-2,3-dihydro-lH-indole (Ig, 92%) as solid.

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

Reference:
Patent; F2G LTD; WO2006/123145; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-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. Formula: C8H6N2O3

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

The synthetic route of 5-Nitroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Pharmacia Corporation; US2003/216410; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;; ; Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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. Computed Properties of C14H16BrNO2

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The synthetic route of N-(6-Bromohexyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
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. 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
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. 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;,
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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O

[00244] A solution of ID (500 mg, 0.99 mmol), Intermediate 2 (147 mg, 0.99 mmol) and glyoxylic acid monohydrate (91 mg, 0.99 mmol) in acetonitrile (2 mL) and DMF (2 mL) was micro waved at 100 0C for 10 min. The reaction mixture was concentrated in vacuo and purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield IE (540 mg, 0.812 mmol, 82% yield) as a yellow foam. MS (ESI) m/z 665.6 (M+H)+.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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.

Argon was purged to a stirring solution of 5-bromoisoindolin-l-one (200 mg, 0.943 mmol) in dimethylformamide for 30 min, to this bis(pinacolato)diboron (477 mg, 1.886 mmol) and tetrakis(triphenylphosphine) palladium(O) (13 mg, 0.018 mmol) and potassium acetate (277 mg, 2.829 mmol) were added and the reaction mixture was heated to 70 C for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was extracted with ethyl acetate (3 x). The combined ethyl acetate layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (100 mg, 41 %).

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H°jland; WO2011/134468; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-23-1,Some common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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 mixture of 4-(6-chloro-pyrimidin-4-yloxy)-piperidine-1 -carboxylic acid isopropyl ester (50.4 mg, 0.168 mmol) and 2,3-dihydro-1 H-indole-5-carbonitrile (22.0 mg, 0.15 mmol) in anhydrous 1 ,4-dioxane (2.0 ml.) was heated to 105 degrees Celsius. After stirring for 5 min, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.184 ml_, 0.184 mmol) was added. After 30 minutes, the reaction mixture was quenched with saturated aqueous ammonium chloride and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous phase was extracted three times with dichloromethane, and the combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the crude residue was purified by column chromatography (20-60% ethyl acetate in heptane) to afford isopropyl 4-{[6-(5-cyano-2,3-dihydro-1 H-indol-1 -yl)pyrimidin-4-yl]oxy}piperidine-1 – carboxylate (38 mg, 61 %) as a white solid. 1H NMR (400 MHz, deuterochloroform) delta 1.25 (d, J=6.25 Hz, 6 H) 1.68 – 1.78 (m, 2 H) 1.96 – 2.04 (m, 2 H) 3.24 – 3.36 (m, 4 H) 3.78 – 3.87 (m, 2 H) 4.03 (t, J=8.79 Hz, 2 H) 4.89 – 4.97 (m, 1 H) 5.29 – 5.36 (m, 1 H) 5.96 (s, 1 H) 7.43 (s, 1 H) 7.51 (dd, J=8.79, 1.17 Hz, 1 H) 8.48 – 8.53 (m, 2 H). LCMS (ES+): 408.4 (M+1 ).

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

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem