Month: August 2021

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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O

[00244] A solution of ID (500 mg, 0.99 mmol), Intermediate 2 (147 mg, 0.99 mmol) and glyoxylic acid monohydrate (91 mg, 0.99 mmol) in acetonitrile (2 mL) and DMF (2 mL) was micro waved at 100 0C for 10 min. The reaction mixture was concentrated in vacuo and purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield IE (540 mg, 0.812 mmol, 82% yield) as a yellow foam. MS (ESI) m/z 665.6 (M+H)+.

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:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.

Argon was purged to a stirring solution of 5-bromoisoindolin-l-one (200 mg, 0.943 mmol) in dimethylformamide for 30 min, to this bis(pinacolato)diboron (477 mg, 1.886 mmol) and tetrakis(triphenylphosphine) palladium(O) (13 mg, 0.018 mmol) and potassium acetate (277 mg, 2.829 mmol) were added and the reaction mixture was heated to 70 C for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was extracted with ethyl acetate (3 x). The combined ethyl acetate layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (100 mg, 41 %).

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H°jland; WO2011/134468; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-23-1,Some common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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.

A mixture of 4-(6-chloro-pyrimidin-4-yloxy)-piperidine-1 -carboxylic acid isopropyl ester (50.4 mg, 0.168 mmol) and 2,3-dihydro-1 H-indole-5-carbonitrile (22.0 mg, 0.15 mmol) in anhydrous 1 ,4-dioxane (2.0 ml.) was heated to 105 degrees Celsius. After stirring for 5 min, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.184 ml_, 0.184 mmol) was added. After 30 minutes, the reaction mixture was quenched with saturated aqueous ammonium chloride and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous phase was extracted three times with dichloromethane, and the combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the crude residue was purified by column chromatography (20-60% ethyl acetate in heptane) to afford isopropyl 4-{[6-(5-cyano-2,3-dihydro-1 H-indol-1 -yl)pyrimidin-4-yl]oxy}piperidine-1 – carboxylate (38 mg, 61 %) as a white solid. 1H NMR (400 MHz, deuterochloroform) delta 1.25 (d, J=6.25 Hz, 6 H) 1.68 – 1.78 (m, 2 H) 1.96 – 2.04 (m, 2 H) 3.24 – 3.36 (m, 4 H) 3.78 – 3.87 (m, 2 H) 4.03 (t, J=8.79 Hz, 2 H) 4.89 – 4.97 (m, 1 H) 5.29 – 5.36 (m, 1 H) 5.96 (s, 1 H) 7.43 (s, 1 H) 7.51 (dd, J=8.79, 1.17 Hz, 1 H) 8.48 – 8.53 (m, 2 H). LCMS (ES+): 408.4 (M+1 ).

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

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); 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 61-70-1 as follows. COA of Formula: C9H9NO

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3335-98-6, 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 3335-98-6 as follows.

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.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15937-07-2, The chemical industry reduces the impact on the environment during synthesis 15937-07-2, name is 5,6-Dimethoxyindoline, I believe this compound will play a more active role in future production and life.

1st Stage 7.1 g of 2-chloro-5-nitropyridine (0.045 mol) were stirred with 8.0 g of 5,6-dimethoxyindoline (0.045 mol) and 4.2 g of sodium hydrogen carbonate (0.050 mol) for 2.5 h at 80 C. in 50 ml of DMSO. After cooling, the mixture was poured onto ice, the precipitate was removed by filtration under suction and the product was dried in vacuo at 45 C. The intermediate product 5,6-dimethoxy-1-(5-nitro-(2-pyridyl)-indoline was obtained in a yield of 23.1% (melting point: 202-207 C.).

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

Reference:
Patent; Naumann, Frank; Hollenberg, Detlef; Hoeffkes, Horst; Rose, David; US2004/6834; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-Nitroindoline, 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 19727-83-4, category: indolines-derivatives

Example 26 6,7-Dimethoxy-4-(6-nitro-2,3-dihydro-indol-1-yl)-quinazoline Utilizing a procedure analogous to that described in Example 1, this product was prepared in 91% yield from 6-nitro-indoline (1 eq.) and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 275 C. (dec); GC-MS: 352 (M+); anal. RP18-HPLC RT: 4.30 min.).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, molecular formula is C8H3F2NO2, 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: 774-47-0

Example 3 2-Amino-4,5-difluorobenzoic acid To a 2 liter four neck round bottom flask equipped with a mechanical stirrer, a condenser and a thermometer was charged 100 g of 5,6-difluoroisatin and 900 ml of aqueous 2.5N sodium hydroxide solution. The mixture was stirred until a homogeneous purple solution resulted. To this solution, and with external cooling (acetone/wet ice), was charged 162 ml of a 30% solution of hydrogen peroxide over a period of about 20 minutes. The reaction temperature never rose above 45C throughout the addition. After addition was complete, the reaction mixture was heated for 2 hours and was then cooled to room temperature. This mixture was then carefully quenched into a solution of 6N HCl (200 ml) in a 5 liter flask. The temperature stayed at about 15-20C throughout the addition. A 5 liter flask was used because of extensive foaming during the quench. The pH of the quench mixture was adjusted from about 5.0 to about 1.0 with concentrated hydrochloric acid as precipitation of the product caused stirring to slow down. To the reaction mixture was then added 260 ml of 50% NaOH solution to bring the pH up to 4.50. The mixture was filtered and the solids were sucked dry. The product was then dried in an oven at 40C and reduced pressure to obtain 95 g of the title compound, m.p. 180-181C. NMR(CDCl3 300 MHz): 7.56 (1H,dd,J=8 Hz, J=7 Hz), 6.68 (1H,dd,J=8 Hz, J=7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 774-47-0, its application will become more common.

Reference:
Patent; PFIZER INC.; EP342849; (1990); A3;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of substituted isatins (1 mmol),cyclic 1,3-diketone (1 mmol), malononitrile (1 mmol)and nano Ag/kaolin (0.085 g, 7 mol%) in EtOH (10mL) was stirred at reflux temperature. Uponcompletion instead of compilation, monitored by TLC(n-hexane/ethyl acetate: 2/1), the reaction mixture wasallowed to cool to room temperature. The catalyst wasseparated by filtration of this solution. The solution wasconcentrated under vacuum to afford the product,which was purified by recrystallization in the ethanol.All the products were identified by comparing of meltingpoint and 1H NMR spectra with those of authenticsamples reported in the literature.2- Amino -5′ – Nitro -2 ‘ , 5- Ioxo -5 , 6 , 7 , 8 -Tetrahydrospiro[Chrom-ene-4,3’-Indoline]-3-Carbonitrile (4c).m.p. 283-285 C; 1H NMR (400 MHz,DMSO-d6) : 1.79 -2.02 (m, 2H, CH2), 2.22-2.26 (m,2H, CH2), 2.62-2.69 (m, 2H, CH2), 7.03 (d, J=8.6Hz, 1H), 7.40 (brs, 2H, NH2), 7.87 (s, 1H, ArH), 8.13(d, J= 6.22 Hz, 1H, ArH), 11.17 (s, 1H, NH).

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sadeghi, Bahareh; Lasemi, Zahra; Azimi, Razieh; Oriental Journal of Chemistry; vol. 31; 2; (2015); p. 1175 – 1179;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem