Month: July 2021

Related Products of 150560-58-0,Some common heterocyclic compound, 150560-58-0, name is 5-Isopropylindoline-2,3-dione, molecular formula is C11H11NO2, 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: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL×4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

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

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-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. Quality Control of 4,7-Dichloroindoline-2,3-dione

Example II-87: (5-Hydroxy-1H-pyrazol-3-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2-dihdyro- indol-3-ylidene]-hydrazide (06I6L (5-HYDROXY-1H-PYRAZOL-3-YL3-ACETIC acid hydrazide (56 mg, 0. 36 mmol) and the isatin (45 mg, 0.30 mmol) were suspended in absolute ethanol (-2-5 mL) in A closed vial and stirred in a 110 C oil bath for 2 days and, if needed, an additional 2 h at 150 C. The warm reaction mixture was evaporated with a stream of nitrogen to about one-fourth volume and acetic acid (-1-3 mL) was added and warmed to partially dissolve the solids. After cooling, the yellow solids were collected and washed with ethanol, and dried. This process was repeated if necessary. [0617] 1HNMR (400 MHz, D6-DMSO) o 12.60 (s, 1 H), 11.85 (s, 1 H), 11.5 (br s, 1 H), 9.5 (br s, 1 H), 7.44 (d, 1 H), 7.16 (d, 1 H), 5.40 (s, 1H), 4.0 (br s, 2H); LCMS-APCI m/z 354 [M+1] +.

The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, INC.; WO2005/5378; (2005); A2;,
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Indoline | C8H9N – PubChem

Reference of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil. Rf = 0.32 (silica gel, hexane/EtOAc = 1/1); 1H NMR (300 MHz, CDCl3) delta 7.83 (d, J = 6.6 Hz, 1H, ArH), 7.56-7.41 (m, 3H, ArH), 5.70 (ddt, J = 6.3, 10.5, 17.1 Hz, 1H, CH),4.97-4.90 (m, 2H, CH2), 4.53 (t, J = 4.2 Hz, 1H, CH), 3.11 (s, 3H, CH3), 2.13-2.00 (m, 2H, CH2), 1.80 (m, 1H,CH2), 1.60 (m, 2H, CH2); 13C NMR (75 MHz, CDCl3) delta 168.5 (C), 144.6 (C), 137.1 (CH), 132.7 (C),131.2 (CH), 128.0 (CH), 123.4 (CH), 121.9 (CH), 115.1 (CH2), 60.9 (CH), 29.7 (CH2), 27.2 (CH3),26.6 (CH2).

The synthetic route of 2-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sengoku, Tetsuya; Nagai, Yuichiro; Inuzuka, Toshiyasu; Yoda, Hidemi; Synlett; vol. 30; 2; (2019); p. 199 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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. Application In Synthesis of tert-Butyl 5-bromoisoindoline-2-carboxylate

5-Bromo-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.97 g, 10 mmol) was azeotropically dried by evaporation from toluene. Tris(dibenzylideneacetone)dipalladium (0) (228 mg, 0.25 mmol), 2-(di-tert-butylphosphino)biphenyl (149 mg, 0.50 mmol) and sodium tert-butoxide (1.34 g, 13.9 mmol) were added and the flask was purged with nitrogen. Toluene (25 ml.) then N-methylpiperazine (1.33 mL, 12 mmol) were added and the mixture was heated to 8O0C for 2 hours. After allowing to cool to r.t. the mixture was diluted with ether, filtered through Celite and concentrated to give a residue that was purified by flash chromatography on silica (2M methanolic ammonia/dichloromethane, 1% to 3% gradient). This afforded the title compound as a brown solid (1.45g, 46%). 1H NMR (MeOH-d4) 7.15 (1H, m), 6.94-6.88 (2H, m), 4.60-4.54 (4H1 m), 3.20-3.17 (4H, m), 2.63-2.60 (4H, m), 2.34 (3H, s), 1.52 (9H, s). MS: [M+H]+ 318.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 a 25 ml round bottom flask, a mixture of isatin / acenaphthoquinone / 2-hydroxynaphthoquinone/ ninhydrin (1 mmol), o-phenylene diamine (1 mmol) in ethanol (95 %, 10 mL) and sulfamic acid (20 mol %) was added. The reaction mixture was stirred at ambient temperature for time mentioned in Table II, monitored by TLC. After completion of reaction, the mixture was filtered washed with ethanol and dried to furnish the desired pure products in high yields.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hegade, Pravin G.; Mane, Mansing M.; Patil, Jayavant D.; Pore, Dattaprasad M.; Synthetic Communications; vol. 44; 23; (2014); p. 3384 – 3391;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C22H19N3O6

Add 4 kg of N,N-dimethylacetamide to a 10 L reaction flask.Add 1.0 kg of compound (II), add 1.4 kg of ethylenediamine, stir and heat.The reaction was stirred at 40 C for 4 h. The reaction solution was cooled to 30 ± 5 C,Add about 1.2kg of phosphoric acid, add the reaction, and cool the reaction solution to 10±5C for 1h~1.5h.Filtration, filter cake washed with N, N-dimethylacetamide, ethanol,The wet product was transferred to a blast oven, and the internal temperature of the oven was controlled to dry at 50-55 C for 16 ± 1 hour to obtain a white solid. Yield: 93%, product purity (HPLC): 99.5%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou Pharmaceutical Factory Co., Ltd.; Guo Yijie; Jin Xiaofeng; Shao Zhichun; (13 pag.)CN110156768; (2019); A;,
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. 337536-15-9, name is 4-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrNO

A suspension of Example 1C (2g, 9.43 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxa-borolan-2-yl)aniline (2.5g, 11.3 mmol), and Na2CO3 (2.2g, 20.8 mmol) in DME (68 mL) andwater (17 mL) was purged with nitrogen, treated with Pd(PPh3)4 (Ig, 0.9 mmol), and stirredat 90 C for 19 hours. The reaction mixture was cooled to room temperature, concentrated toone-third its original volume, diluted with ethyl acetate (30 mL) and water (20 mL), andfiltered. The filter cake was washed with water and ethyl acetate and dried to give 1.25g ofthe desired product.

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/108672; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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. category: indolines-derivatives

Under argon atmosphere conditions, add 0.0133 g (0.10 mmol) of 2-methylindolinoline (1a), 0.0013 g (0.002 mmol) of acid eosin EosinY, 0.150 g of Antarctica lipase CAL-A, 0.0146 g (0.10 mmol) of n-octyl mercaptan, 0.104 g (0.50 mmol) of allyl-3-methoxyphenyl carbonate (2b), methyl tert-butyl ether (TBME) 2.0 mL;The reaction was stirred at 45 C for 6 hours under a 6w white light. After the reaction, the insoluble enzyme was removed by suction filtration, the solvent was distilled off under reduced pressure, and the solvent was separated by column chromatography. The eluent: (V) petroleum ether / (V) Ethyl acetate = 30/1. 0.0189 g of a yellow liquid product (3ab) was obtained with a product yield of 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6872-06-6, its application will become more common.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (16 pag.)CN110437123; (2019); A;,
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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C21H21N3O5

100 g (R)-2-(2-hydroxy-3-(4-(3-oxo-morpholino) phenyl amino) propyl) isoindoline-i ,3-dione of Formula (F) and MDC (i000 ml) were added to REF at 25 C. to 35 C. and heated to 40 C. to 45 C. Further, 6i g N,N-Carbonyl diimidazole (CDI) and 0.5 g DMAP were added and stirred for 3-4 hours. Excess MDC was evaporated under, reduced pressure. The reaction mass was cooled to 25 C. to 35 C. followed by addition of dilute HC1 solution and stirred for i hour and finally filtered and washed with 2×200 ml water to afford title compound as (S)-2-((2-oxo-3-(4-(3-oxo-mor- pholino)phenyl)oxazolidin-5-yl)methyl)isoindoline- i ,3-di- one of Formula (I).Excess MDC was evaporated under, reduced pressure. The reaction mass was cooled to 25 C. to 35 C. followed by addition of dilute HCl solution and stirred for 1 hour and finally filtered and washed with 2*200 ml water to afford title compound as (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I).

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 446292-07-5.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Oxoindoline-5-carboxylic Acid

To a stirred solution of 2-oxoindoline-5-carboxylic acid (0.7 g, 3.95 mmol) in DMF (5 mL) was added EDCI.HCl (1.13 g, 5.92 mmol), HOBt (0.8 g, 5.92 mmol) and triethylamine (1.7 mL, 11.8 mmol). The solution was stirred for 10 min at 0oC. After that tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (0.93 g, 4.34 mmol) was added and the reaction stirred at rt for 16 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain a crude residue which was purified by preparative HPLC to afford tert-butyl 4-((2-oxoindoline-5- carboxamido)methyl)piperidine-1-carboxylate (0.130 g, 8%)

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem