Month: April 2021

Application of 446292-07-5, 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. 446292-07-5 name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, 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.

Compound I was added to 39.5 g (0.1 mol), N,N-dimethylaniline 19.4 (0.16 mol), trichloromethane 120ml, added to 250ml of three bottles, stir to dissolve the solid. cooling to -20 C, temperature control at -20C ~ 10C slowly into the phosgene about 10.9g (0.11mol), and then heat for 10h. Nitrogen was bubbled through for 15 minutes. The crude product of the compound of formula (II) was obtained by distilling off the trichloromethane under reduced pressure by heating under reduced pressure, Filtration and drying gave 41.1 g of the compound of formula (II) as a white solid in 97.6% yield. HPLC, the purity was 98.95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Chongqing Ying Sikai Chemical Co., Ltd.; Chongqing Kerui Pharmaceutical (Group) Co., Ltd.; Huang Yuming; Wu Mingliang; Long Ping; Cheng Peng; Li Yang; Liu Junmin; Yue Xuerong; (10 pag.)CN106588905; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8 Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8 Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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

Preparation of 3- {7-cyano-5 – [(2R) -2 – ({2- [2- (2,2,2- trifluoroethoxy) phenoxy] ethyl} Propyl benzoate fumaric acid salt A mixture of 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H- (2R, 3R) -monotartaric acid salt (monotartaric acid salt of the compound of formula (2)), potassium carbonate (80 g), and a mixed solvent of acetonitrile and dimethylacetamide ACN / DMAC = 500 mL / 500 mL) was warmed to 80 & lt; 0 & gt; C and stirred for 30 min. To the reaction mixture, 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula (III)) and 9.70 g of KI were added, Lt; / RTI & gt; The reaction mixture was cooled to room temperature and extracted with 1 L of ethyl acetate and 1.5 L of water. The organic layer obtained by layer separation was washed with 1 L of brine, dried over 40 g of anhydrous MgSO4 for 30 minutes, and then washed again with 200 mL of ethyl acetate. 23 g of fumaric acid was added to the obtained organic layer, and the mixture was heated to 50 DEG C, cooled to room temperature, and stirred for 2 hours. reaction The mixture was filtered, and the resulting solid was washed with 200 mL of ethyl acetate and dried in vacuo to yield 113 g of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 239463-85-5, its application will become more common.

Reference:
Patent; Dasan Medichem Co., Ltd; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Jo, Hey Jung; Moon, Sung Chul; Aum, Woon Yong; Kim, Jae Hyung; (12 pag.)KR2016/27536; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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

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¡Á3). 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

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24566-79-8, its application will become more common.

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

Related Products of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, 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 61-70-1, Formula: C9H9NO

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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, 1-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxyindolin-2-one

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

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:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 924304-73-4, 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. 924304-73-4, name is 4-Chloroisoindoline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: Synthesis of (3J?,5S)-1-((S)-4-(but-3-enyIoxy)-2-(tert- butoxycarbonylamino)butanoyl)-5-((li?,25)-1-(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chIoroisoindoline-2-carboxylate[0489] (17?,25)-ethyl l-((25,4i)-1-((5)-4-(but-enyloxy)-2-(tert- butoxycarboalphaylamino)butanoyl)-4-hydroxypyrrolidine-2-carboxamido)-2- vinylcyclopropanecarboxylate (0.55 g, 1.1 mmol) in THF (20 mL) was added 1,1 ‘- carbonyldiimidazole (0.204 g, 1.26 mmol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2- amine (0.92 mL, 5.3 mmol), followed by 4-chloroisoindoline hydrochloride (0.258 g, 1.37 mmo.). The reaction was stirred at 50 C for 18 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (HexanerEthyl acetate=l :3) to give (3i?,5?)-1-((S)-4- (but-3-enyloxy)-2-(tert-butoxycarbonylamino)butanoyi)-5-(( IR,2S)- 1 -(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate as white solid (0.49 g, 66%). MS: Calcd.: 702.3; Found: [M+H]+ 703.1.

The chemical industry reduces the impact on the environment during synthesis 4-Chloroisoindoline hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA, INC.; WO2008/137779; (2008); A2;,
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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H11NO

12 g of compound obtained in the preceding step are heated at 140 C. for 3 h in HBr (48%, 200 ml). After cooling to AT, filtering, the filtrate is concentrated dry. The residue is washed with acetone and dried. 14.8 g of desired product are obtained and used as such.

The synthetic route of 21857-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEREP; US2009/233910; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: C10H9Cl2NO

119 ml (90.1 g, 0.698 mols, 3.21 molar equivalents) of N,N-diisopropylethylamine, 500 ml of acetonitrile and 55.8 g (0.218 mols, 1.0 molar equivalents) of 3-(l- piperazinyl) -1, 2-benzisothiazole hydrochloride (addition salt of compound of formula (III) and hydrochloric acid) are added into a beaker equipped with a magnetic stirrer. The resulting suspension is stirred for 10 minutes. At this point 50 g (0.217 mols, 1.0 molar equivalent) of 5- (2-chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one (Compound of formula (II) wherein X is chlorine) and 0.26 g (1.174 mmols, 0.008 molar equivalents) of NaI are added. The resulting brown suspension is charged into a 1 L reactor vessel, which is heated to 121-122 C (internal pressure increases to 200 kPa) for 25 hours. The reaction is cooled to room temperature and filtered. The solid is washed with acetonitrile, and 56 g of a wet solid are obtained. –> The resulting wet solid is stirred with 4 volumes of water at reflux temperature for 1 h to remove inorganic salts. The suspension is cooled to room temperature and filtered. The solid is washed with water. Ziprasidone base is obtained in 56% molar yield and the purity is 97.8% by HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118289-55-7, its application will become more common.

Reference:
Patent; MEDICHEM, S.A.; WO2006/34964; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem