Author: Jessica.F

Synthetic Route of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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.

Step 11b, Example 26b: (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 42 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 22 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.2 ml of pyridine, and then 33 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water, then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (18 mg) in the form of a pulverulent solid (yield=31%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=+19 C.=0.950 mg/0.5 ml in DMSO

Statistics shows that 4-Chloroindoline is playing an increasingly important role. we look forward to future research findings about 41910-64-9.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 15362-40-0,Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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 four-necked flask was added compound IV (233 g, 0.84 mol), potassium hydroxide (94.3 g, 1.68 mol), 10% hydrochloric acid 668 mL, zinc hydroxide (167 g, 1.68 mol), and the temperature was raised to 85 C for 8 hours , Cooling to 60 ~ 65 , vacuum filtration, filter cake and add a small amount of water to get 499.5g (compound I: diclofenac zinc), the yield of 91%.

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Liaoyuan Yinying Pharmaceutical Co., Ltd.; Li Guiying; Wang Zhaokun; Li Shumei; Peng Xiaojuan; Jin Xingtong; (8 pag.)CN106905178; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7223-50-9, name is N-Propargylphthalimide, 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 7223-50-9, category: indolines-derivatives

N-propargyl phtalimide (0.64 g; 3.4 mmol) is dissolved in 1,4-dioxane (20 mL), then dimethylamine (8.5 mL; 17 mmol), copper (I) chloride (0.35 g) and paraformaldehyde (1g) are added. The solution is refluxed for 3h. After cooling at room temperature the formed precipitate is filtered off and the filtrate is evaporated under vacuum to give a green oily residue that, after dissolution in CH2Cl2, is washed with sat. sol. NaHCO3 (2×30 mL) and water (2×30 mL). The organic phase is dried over Na2SO4 and evaporated under vacuum. The crude product is purified by treatment with diethyl ether to give N-phtalimido-N’,N’-dimethylbutin-2-yl-1,4-diamine as pale yellow solid (0.5 g; 2.05 mmol).

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, N-Propargylphthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dompe farmaceutici s.p.a.; ALLEGRETTI, Marcello; BERTINI, Riccardo; BERDINI, Valerio; BIZZARRI, Cinzia; CESTA, Maria, Candida; DI CIOCCIO, Vito; CASELLI, Gianfranco; COLOTTA, Francesco; GANDOLFI, Carmelo; (32 pag.)EP1366018; (2016); B1;,
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. 56341-37-8, name is 6-Chlorooxindole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6-Chlorooxindole

Compound 1 (62 mmol) and Compound 2 (60 mmol) were dissolved in 200 mL of methanol.After the dissolution was sufficient, piperidine (12 mmol) was added, and the mixture was refluxed at 70 C.After 5 hours, it was cooled to room temperature and stirred overnight.After the reaction is completed, the suspension is filtered.The obtained solid was washed three times with methanol and dried to give a yellow solid.Compound 3 data:

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 56341-37-8.

Reference:
Patent; South University of Science and Technology of China; Xu Jing; Ning Chengqing; Huang Hengjun; (47 pag.)CN108864113; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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

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

Reference of 32372-82-0,Some common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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.

Isoindoline hydrochloride (31.1 mg, 0.2 mmol), molybdenum disulfide (4 mg, 0.025 mmol) and a stir bar were placed in a reaction tube. After the inert gas was replaced, 1 ml of DMF was added to seal the reaction tube. . The reaction tube was placed in a 150 C oil bath reaction pot, and the reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration, the filtrate was diluted with 15 mL of water, and extracted with ethyl acetate three times, each time 15 mL; The organic product was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate: petroleum ether = 1:3 (1% triethylamine). Black oil, yield 85%.

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

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Ma Juan; (19 pag.)CN107827817; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 897957-06-1, A common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, molecular formula is C9H8BrNO, 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 6-bromo-1-methyl-1 ,3-diotahydro-iotandol-2-one (226 mg, 1 0 mmol) in DMF (6 0 mL) was added zinc cyanide (117 mg 1 ,0 mmol). Then the reaction mixture was degassed and placed under an argon atmosphere and tetrakiotas(triotaphenylphosphiotane)palladiotaum(0) (115 mg, 0 1 mmol) was added The reaction was then placed at 95 C for 100 minutes, at which time it was cooled to room temperature, and diluted with saturated aqueous sodium bicarbonate and dichloromethane The layers were separated and the aqueous layer was extracted two additional times with dichloromethane The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%) to furnish 1- methyl-2-oxo-2,3-diotahydro-1 H-iotandole-6-carboniotatnle, MS. (ES+) m/z 173 0 (M+H)*

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

341988-36-1, name is Methyl indoline-6-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. name: Methyl indoline-6-carboxylate

A solution of methyl indoline-6-carboxylate ( 0.830 g, 4.68 mmol) in dry tetrahydrofuran ( 20 mL ) was treated at 23 0 C and under nitrogen with lithium aluminum hydride ( 0.23 g, 6.08 mmol) and the resulting mixture was stirred for 3.5 h. The reaction mixture was carefully quenched by successive addition of ethyl acetate ( 1 mL ), water ( 0.2 mL), 15 percent aqueous sodium hydroxide ( 0.2 mL ) and water ( 0.6 mL ). The solid formed was filtered and the filtrate was concentrated under reduced pressure. Chromatography of the residual oil on silica gel ( elution ethyl acetate ) followed by distillation under vacuum ( bulb to bulb distillation, bp 95 – 105 ¡ã C / 0.1 torr, air bath temperature ) gave 0.460 g ( 57 percent yield ) of a clear oil which crystallized to a white solid. HPLC (Method A): 0.132 min. HRMS (ESI) calcd for C9Hi2NO [M+H]+ m/z (0724) 150.0913, found 150.0932. NMR (CDC13, 400 MHz) delta ppm: 7.4 (d, J = 7.4 Hz, 1H), 6.66 (dd, J = 7.4, 1.5 Hz, 1H), 6.63 (br. s, 1H), 4.55 (s, 2H), 3.54 (t, J = 8.4 Hz, 2H), 2.99 (t, J = 8.4 Hz, 2H).

The synthetic route of 341988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BANVILLE, Jacques; (230 pag.)WO2016/134450; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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 169037-23-4, Computed Properties of C9H4F3NO3

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
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. 2058-74-4, name is 1-Methylisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 2058-74-4

General procedure: A mixture of 20 mmol of isatine 1a-1f, malononitrile (2), 5,5-dimethylcyclohexane-1,3-dione (3) or 8-hydroxyquinoline (4) and 1 mL of aqueous trimethylamine in 80 mL of ethanol was stirred under reflux for 2 h, after which 40 mL of the solution was distilled off, and the remaining solution was left to stand in the cold. The crystals that formed were filtered off and recrystallized from ethanol.

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; Harutyunyan, A. A.; Pogosyan, M. V.; Pogosyan, S. A.; Russian Journal of Organic Chemistry; vol. 56; 2; (2020); p. 213 – 217; Zh. Org. Khim.; vol. 56; 2; (2020); p. 204 – 209,6;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem