Month: January 2021

Application of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

7-Fluoroisatin (1 mmol) was added to the microwave reaction tube,4-hydroxycoumarin (1.1 mmol),Tetrabutylammonium chloride (0.1 mmol) and water (4 mL),Microwave power 400W,60 radiation 15min,Stop microwave radiation,Cool to room temperature,Vacuum suction filtration,The filter cake was washed with ice-ethanol (0.5 ml)Drying under reduced pressure,A white solid,Yield 94%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroisatin, its application will become more common.

Reference:
Patent; Zunyi Medical College; Zhang Lei; Wang Jing; Liu Lai; Zheng Chengyue; Wang Yang; (4 pag.)CN107098888; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 774-47-0, The chemical industry reduces the impact on the environment during synthesis 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: In an ordinary vial equipped with a Teflon-coated stir bar, thiourea IV or V (0.04 mmol, 11.89 mg, 20 mol %) was dissolved in 1.0 mL of THF. Then the corresponding isatins 1 (0.1 mmol, 1.0 equiv) was added, followed by the addition of alpha,beta-unsaturated ketones 2 (0.2 mmol, 2.0 equiv). The vial was capped with a rubber stopper and the mixture was stirred at room temperature for the time given in the tables. The crude mixture was then purified by flash column chromatography silica gel, using hexane/ethylacetate 2:1 as the eluent. Solvent was removed in vacuo to give the desired products.

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, 5,6-Difluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Guo-Gui; Zhao, Hua; Lan, Yu-Bao; Wu, Bin; Huang, Xiao-Fei; Chen, Jian; Tao, Jing-Chao; Wang, Xing-Wang; Tetrahedron; vol. 68; 20; (2012); p. 3843 – 3850;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

5332-26-3, name is 2-(Bromomethyl)isoindoline-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. Quality Control of 2-(Bromomethyl)isoindoline-1,3-dione

Dimethyl (phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3-hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6 H), 4.12 (d, J=11.4 Hz, 2 H), 7.76 (m, 2 H), 7.87 (m, 2 H).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MethylGene, Inc.; US6884791; (2005); B2;,
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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 6-Methoxyindoline-2,3-dione

General procedure: Similar to as described in General Procedure Z, 6-methoxy-2,3-dihydro- 1H-indole-2,3-dione was converted to the title compound as a yellow solid (600 mg, 10%). LC-MS (ES, m/z): 207 [M+H]; A solution of 2,3-dihydro-1H-indole-2,3-dione (1 eq.) and sodium hydroxide (1.1 eq.) in water was stirred for 5-30 mm at 25 C. Then a solution of sodium nitrite (1 1 eq.) in water and concentrated sulfuric acid (2 eq.) were added dropwise with stirring at 0.-10 C. After 5-30 mm a solution of SnC12 (2.5 eq.) in concentrated hydrochloric acid (15-30 eq.) was added slowly. After5 being stirred for 1–5 h at 25 C the reaction mixture was filtered and the solid was dissolved in methanol. Sulfuric acid (0.5-1 eq.) was added to the solution and the solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum to give the ester which may need further purification such as fresh chromatography.

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 400727-63-1, 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. 400727-63-1, name is tert-Butyl 5-nitroisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with tert-butyl 5-nitroisoindoline-2-carboxylate (650 mg, 2.5 mmol) and C2H5OH (50 mL). This solution was hydrogenated with Pd/C (160mg) at room temperature for 15 h. It was then filtered and the filtrate was concentrated under reduced pressure to afford 231c as a yellow oil (585 mg, 99%), which was used in the next step without further purification. MS: [M+H]+ 179.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5-nitroisoindoline-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. COA of Formula: C8H4BrNO2

General procedure: 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3P04 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2C12or Pd(dppf)2C12 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130¡ãC. The reaction mixture was cooled to rt, diluted with EtOAc (-10 mL/mmol substrate) and filtered through Celite?. The organic solution was washed with brine (-10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2 x). The combined organic layers were dried over MgSO4, filtered andconcentrated in vacuo to give the crude product which was purified as specified below.

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

Reference:
Patent; ISIS INNOVATION LIMITED; CHRISTOU, Ivy; CROSS, Rebecca Lillian; GIANELLA-BORRADORI, Matteo; GREAVES, David Robert; RUSSELL, Angela Jane; WYNNE, Graham Michael; WO2013/41859; (2013); A1;,
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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 5-aminoindoline-1-carboxylate

To a solution of 300mg (1.28mmol) of the compound obtained in the Manufacturing Example 2 in 10mL of anhydrous dichloromethane were added 191muL (2.69mmol) of acetyl chloride and 375muL (2.69mmol) of triethylamine, and the mixture was stirred for 1 hour at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was dried over with anhydrous sodium sulfate and removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1 to 1/2) to give 370mg (quantitative) of the title compound.

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 129487-92-9.

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3339-73-9, These common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, 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: PhB(OH)2 (6 mg, 0.05 mmol), and xylene (10 mL) were added to a round-bottom flask (100 mL), 1a (90 mg, 0.5 mmol), 2a (97 mg,0.5 mmol). A pressure equalising dropping funnel, in which 4 A molecular sieves (6 g) were placed, was installed onto the flask. Then a condenser was connected to the dropping funnel. After refluxing under stirring for 10 h, the reaction mixture was cooled down to room temperature, and evaporated to remove solvent. The resulting residuewas dissolved in EtOAc (20 mL), and then sequentially washed with 0.1 M NaOH (20 mL), water (20 mL), and brine (20 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was subjected to preparative TLC (eluted with PE/acetone (2/1, v/v), Rf = 0.43) to afford ethyl 2-(N-phenyl-2-(N-phenylacetamido)acetamido)acetate 3a (128 mg 72%) as a pale yellow oil.

Statistics shows that 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid is playing an increasingly important role. we look forward to future research findings about 3339-73-9.

Reference:
Article; Huang, Wenhua; Sha, Wen-Bin; Journal of Chemical Research; vol. 37; 8; (2013); p. 460 – 463;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1504-06-9, 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. 1504-06-9 name is 3-Methyloxindole, 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.

3-methylindolin-2-one (441 mg, 3 mmol) in acetonitrile (5 mL) was cooled to 15C. NBS (534 mg,3 mmol) was added. After stirring for 1 h, the reaction was diluted with water (10 mL) and extractedwith EtOAc (20 mL) for three times. The combined organic phase was washed with brine, dried overNa2SO4 and concentrated under reduced pressure to give a residue which was purified by silica gelcolumn chromatography to afford compound 1b (454 mg, 67%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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 (2S,4R)-BOC-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight. The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+H)+; calcd for C20H26BrN2O6: 471.1].

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Holloway, M. Katharine; Liverton, Nigel J.; Ludmerer, Steven W.; McCauley, John A.; Olsen, David B.; Rudd, Michael T.; Vacca, Joseph P.; McIntyre, Charles J.; US2007/27071; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem