Tag: M.W=100-200

Application of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 20 mL two-necked flask was evacuated and backfilled with molecular oxygen. Then, substrate (1 mmol) and 5 mL of PMAS/Au NPs solution (Au: 0.05 mmol, 5 mol %) were added at room temperature. The mixture was stirred at 80 C under molecular oxygen for 4 h. The reaction mixture was extracted with ethyl acetate. The organic layer was evaporated and examined by 1H NMR analysis (JEOL ECS-400, 400 MHz) with 1,3,5-trimethoxybenzene as an internal standard.

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

Reference:
Article; Amaya, Toru; Ito, Tsubasa; Inada, Yuhi; Saio, Daisuke; Hirao, Toshikazu; Tetrahedron Letters; vol. 53; 45; (2012); p. 6144 – 6147,4;,
Indoline – Wikipedia,
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Synthetic Route of 5428-09-1, 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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The optimized hydroformylation?Biginelli reactions were performedby charging an autoclave with [Rh(CO)2acac] (2.60 mg,10.0 mumol 0.25 molpercent), Xantphos (57.9 mg 100 mumol, 2.5 molpercent),and urea (2, 132 mg, 2.2 mmol, 1.1 equiv) as solids under an atmosphereof argon. Subsequently, a solution of the alkene (4 mmol, 2equiv), ethyl acetoacetate (3, 0.25 mL, 260 mg, 2 mmol, 1 equiv)and concd HCl (40 muL) in EtOH (4 mL) was prepared and thentransferred into the autoclave via syringe. The autoclave was purgedthree times with syngas (CO/H2, 1:1), pressurized at 20 bar, andplaced in a preheated aluminum block at 100 °C. The reactions werestopped after 24 h by cooling the autoclave in a water bath (18 °C),venting and purging with argon. To the crude reaction mixture1,3,5-trimethoxybenzene (33.6 mg, 0.20 mmol, 0.1 equiv) as internalstandard was added and the suspension dissolved in CH2Cl2 (5mL). After evaporation of the solvents the crude product was analyzedby NMR spectroscopy and purified via flash chromatographyto yield the pure 3,4-dihydropyrimidin-2(1H)-ones 6a?l as colorlesssolids or foams

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-Allylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuchs, Daniela; Nasr-Esfahani, Mahboobeh; Diab, Lisa; Smejkal, Tomas; Breit, Bernhard; Synlett; vol. 24; 13; (2013); p. 1657 – 1662;,
Indoline – Wikipedia,
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Reference of 114041-16-6,Some common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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.

Compound 250:2-chloropyrimidine derivative 249 (50 mg) and isoindoline (50 mg) were dissolved in Acetonitrile (5 mL) and the mixture was heated to 80 C and stirred for 1 hour. The solvent was removed by concentration and the residue was purified by Prep-LC gave compound 250. HPLC-MS tR = 1.63 min (UV254 nm); mass calculated for formula 029H35N7O5 561.3, observed LCMS m/z 562.3 (M+H).

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 480-91-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 480-91-1 name is Isoindolin-1-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

At 0 C., 611.3 mg (15.3 mmol, 60% pure) of sodium hydride were added to 2.035 g (15.3 mmol) of 1-oxoindoline in 12 ml of DMF. The mixture was stirred for 30 min, and 6.0 g (12.7 mmol) of tert-butyl(+/-)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0 C. The reaction mixture was stirred for a further 4 h, water was then added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The crude product was treated with diethyl ether in an ultrasonic bath and the solid was isolated by filtration. This gave 3.40 g (60.2% of theory) of the target compound.LC-MS (method 11): Rt=1.57 min; m/z=350 (M-C4H8+H)+.1H-NMR (400 MHz, DMSO-d6): delta=7.72 (d, 1H), 7.60-7.50 (m, 3H), 7.30 (d, 2H), 7.21 (d, 2H), 4.71 (s, 2H), 4.38 (s, 2H), 3.18 (d, 1H), 2.35 (m, 1H), 1.85-1.37 (m, 5H), 1.34 (s, 9H), 1.20 (m, 2H), 0.91 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIEGESELLSCHAFT; US2011/34450; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, 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 1074-82-4 as follows.

Into a reaction vessel were put potassium phthalimide (5.00g, 27.0mmol), benzyltrimethylammonium chloride (0.50g, 2.70mmol) and tert -buyl alcohol (50ml) and then thereto was added (S)-epichlorohydrin (6.53g, 54.0mmol). The mixture was stirred at 20C for 24 hours and the solvent was removed. To the residue was added ethyl acetate (30ml), the mixture was washed with water (20ml), and then ethyl acetate was removed to give crude (S)-glycidylphthalimide (3.95g, yield: 72%, optical purity: 97%e.e.) as a white solid.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAISO CO., LTD.; EP1403267; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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 malononitrile (1 mmol), isatin (1 mmol), dicarbonyl (1 mmol), PEGOSO3H(0.1 mmol), and water (2 mL) was stirred under reflux for the appropriate time (shown in Tables 3, 4). After completion of the reaction, the reaction mixture was filtered and the residue was washed with ethanol. The crude solid product was recrystallized from EtOH to afforded the pure products in high purity and yield.Assignment of the structures of the products was based on their 1H NMR, 13C NMR,and IR spectra.

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; Nasseri; Zakerinasab; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5261 – 5270;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 141452-01-9, These common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, 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 solution of 17 (0.28 g, 1.58 mmol) in pyridine (2 mL) was added 4-methoxybenzenesulfonyl chloride (0.32 g, 1.58 mmol) and heated to reflux for 6 h. The reaction mixture was purified by chromatography over silica gel to afford 18c as a white solid (85% yield; 1:1 EtOAc/n-hexane): 1H NMR (300 MHz, CDCl3) delta 2.96 (t, J=8.7 Hz, 2H), 3.80 (s, 3H), 3.85 (s, 3H), 3.93 (t, J=8.7 Hz, 2H), 6.89 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.4 Hz, 1H), 7.20-7.76 (m, 3H), 7.88 (d, J=8.4 Hz, 1H).

Statistics shows that Methyl indoline-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 141452-01-9.

Reference:
Patent; Taipei Medical University; Liou, Jing-Ping; Lin, Chien-Huang; Pan, Shiow-Lin; Yang, Chia-Ron; Teng, Che-Ming; US2015/368195; (2015); 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 25369-33-9 as follows. name: 7-Chloroindolin-2-one

To a suspension of AlCl3 (13.4 g, 0.10 mol) in methylene chloride (40 mL) is added a solution of 7-Chlorooxindole (0.10 mol) and chloroacetyl chloride (8 mL, 0.10 mol) at 0 C. The solution is warmed to ambient temperature for two hours and poured onto ice and extracted with methylene chloride, washing with saturated bicarbonate solution, brine, and drying over MgSO4 would provide the desired chloroketone.

According to the analysis of related databases, 25369-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, 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: 21857-45-4

To a solution of 5-methoxyindoline (175 mg, 1.17 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (55%, 70 mg, 1.6 mmol) at 0 C. After the reaction mixture was stirred at the same temperature for 30 min, (2-bromoethyl)benzene (0.22 mL, 1.6 mmol) was added with additional stirring at room temperature overnight. After the reaction mixture was quenched with water at 0 C., the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain 5-methoxy-1-phenethylindole (95 mg, 32%).

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

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 912999-79-2, name is 5-Chloroisoindoline hydrochloride, molecular formula is C8H9Cl2N, 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. Recommanded Product: 912999-79-2

A mixture of Compound 151A (340 mg, 2.36 mmol) and 1-(azidomethyl)-4- methoxybenzene (500 mg, 3.07 mmol) in toluene (15 mL) was stirred at 110 C for 48 hours. The reaction mixture was concentrated and purified by column chromatography on silica gel using ethyl acetate- hexane as eluent to afford a Mixture 151B. LC-MS (ESI) m/z: 278 [M+H]._A Mixture 151B (60 mg, 0.217 mmol) and thionyl chloride (0.45 mL) in methylene chloride (10 mL) was stirred at 50 C for 5 hours. The reaction mixture was concentrated to give isic, which was used directly in the next step without further purification.LC-MS (ESI) m/z: 296 [M+H]._ A Mixture 151C (74 mg, 0.2 17 mmol), 5-chloroisoindoline (38 mg, 0.248 mmol), and K2C03 (60 mg, 0.43 5 mmol) in DMF (6 mL) was stirred at 60 C for 5 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC to afford a Mixture 151D. LCMS (ESI) m/z: 413 [M+H]t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 912999-79-2, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem