Month: February 2021

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 169037-23-4

General procedure: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Huang; Xu, Yong; Mao, Fei; Zhu, Jin; Jiang, Hualiang; Li, Jian; Tetrahedron Letters; vol. 56; 4; (2015); p. 586 – 589;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2307-00-8, 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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 110 2-METHYL-5-[(2-OXO-1-PHENYL-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)AMINO]-2H-ISOINDOLE-1,3(2H)-DIONE A mixture of 1-phenylisatin (50 mg, 0.22 mmol) and 4-amino-N-methylpthalimide (40 mg, 0.22 mmol) was heated neat at 215 C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product as a yellow solid (8 mg, 0.02 mmol, 10%). 1H NMR (400 MHz): delta 7.88 (d, J=7.8, 1H), 7.83-7.80 (m, 1H), 7.51 (t, J=7.5, 1H), 7.47-7.18 (m, 6H), 7.02 (t, J=8.0, 1H), 6.91-6.79 (m, 2H), 6.58 (d, J=7.5, 1H), 3.22 (s, 3H) ESI-MS m/z found 382 (MH+).

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-Amino-2-methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Konkel, Michael; Werzel, John M.; Talisman, Jamie; US2004/102507; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 7699-18-5, 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 7699-18-5 as follows.

Preparation of 5-methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)-indole-3-carbaldehyde; 5-Methoxy isatin (0.2 g, 1.1 mmol, 1 eq.) was dissolved in hydrazine hydrate (1.2 ml_, 38 mmol, 34 eq.) and refluxed for 15 minutes. The reaction mixture was poured into cold water and extracted with EtOAc. The combined organic extracts were dried on Na2SO4. The solvent was evaporated to afford crude 5-methoxy-1 ,3-dihydro-indol-2-one that was purified by silica gel column chromatography (eluent: hexane/EtOAc from 10:0 to 6:4). Yield: 27%. MS (m/z): 164.2 (MH+).Phosphorous oxybromide (0.35 ml_, 3.1 mmol, 2.5 eq.) was added drop wise to a solution of DMF (0.3 ml_, 3.7 mmol, 3 eq.) in dry methylene chloride at 00C. The mixture was stirred at 00C for 30 minutes, then a solution of 5-methoxy-1 ,3-dihydro-indol-2-one (0.2 g, 1.2 mmol, 1 eq.) in dry methylene chloride (2 ml_) was added and the mixture was refluxed for 3 hours. The solution was neutralized with solid NaHCO3 and extracted with methylene chloride. The organic layer was dried on Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by silica gel column chromatography (eluent: hexane/AcOEt 6:4 to 4:6) to give pure 2-bromo-5-methoxy-indole-3-carbaldehyde. Yield: 45%. MS (m/z): 254.1 (MH+). A stirred solution of 2-bromo-5-methoxy-indole-3-carbaldehyde (2.0 g, 7.9 mmol, 1 eq.) in DME (2 ml_) was deoxygenated by bubbling argon for 10 minutes at rt. Pd(PPh3)4 (0.9 g, 0.8 mmol, 0.1 eq.) was added followed by a solution of 1-methyl-4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazole (2.4 g, 1 1.63 mmol, 1.48 eq.) in ethanol (2.5 ml_). 2M Na2CO3 (33 ml_, 8.5 eq.) was also deoxygenated with argon and added. The resulting mixture was heated at 78C for 18 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted with methylene chloride. Organic layer was dried on anhydrous Na2SO4 and evaporated under reduced pressure to give the crude product 1f. Yield: 89%. MS (m/z): 256.1 (MH+).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.; WO2010/30727; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 6-bromooxindole (Procedure D, 0.50 g, 2.4 mmol), vinyltributylstannane (0.95 g, 3.0 mmol), lithium chloride (0.03 g, 7.1 mmol), 2,6-di-tert-butyl-4-methylphenol (0.01 g, 0.05 mmol) in acetonitrile (25 ml) stirring at 80 C. was added dichlorobis(triphenylphosphine)palladium (II). The resulting reaction was stirred with heating for 16 h. The reaction was poured into a vigorously stirring mixture of 5M potassium fluoride solution: ethyl acetate/ 1:1 (250 mL) and stirred for 0.75 h. The resulting biphashic mixture was filtered through a Celite 521 pad and the pad flushed with ethyl acetate (5¡Á2 mL). The combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL) and filtered through Whatman PS 1 paper and evaporated in vacuo to a golden yellow syrup. The syrup was titurated with diethyl ether to yield several crops of tan solid. Pure samples were combined, slurried with diethyl ether, filtered, and air dried to yield 0.12 g (31%) of 6-vinyloxindole: 1H NMR (DMSO-d6): delta 10.36 (s, 1H), 7.13 (d, 1H, J=7.7 Hz), 6.98 (d, 1H, J=7.5 Hz), 6.66 (dd, 1H, J=10.9, 17.7 Hz), 5.70 (d, 1H, J=17.6 Hz), 5.18 (d, 1H, J=10.9 Hz), 3.42 (s, 2H).

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, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-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. Formula: C9H9NO2

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 5-Methoxyindolin-2-one 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

Electric Literature of 106976-23-2, These common heterocyclic compound, 106976-23-2, name is 5-Bromo-6-methylindoline-2,3-dione, 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 5-bromo-6-methyl-indoline-2,3-dione (980 mg, 4.08 mmol) in tetrahydrofuran (50 mL) at 0 C. was added NaBH4 (124 mg, 3.26 mmol). The mixture was stirred at 0 C. for 10 min. H2O (50 mL) was added and the mixture extracted with EtOAc (3*200 mL). The combined extracts were washed with brine (100 mL), dried with Na2SO4, filtered and concentrated to give crude 5-bromo-3-hydroxy-6-methyl-indolin-2-one (650 mg, 2.5 mmol, 61% yield) as a brown solid. LCMS (ESI) [M+Na]+=265.9.

Statistics shows that 5-Bromo-6-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 106976-23-2.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); 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 21857-45-4 as follows. Safety of 5-Methoxyindoline

General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3¡Á20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.

According to the analysis of related databases, 21857-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Ci-Ping; Jiang, Guo-Fang; Tetrahedron Letters; vol. 58; 18; (2017); p. 1747 – 1750;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21857-45-4, 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 21857-45-4 as follows.

To a solution of 5-methoxyindoline (180 mg, 1.21 mmol) in 3.6 mL of acetic acid was added 3,3-dimethylbutylaldehyde (0.18 mL, 1.4 mmol) and sodium cyanoborohydride (190 mg, 3.0 mmol) at room temperature, successively. After the reaction mixture was stirred for 2 h, the reaction mixture was basified by saturated NaHCO3 aqueous solution and the solution was extracted with ethyl acetate (20 mL). The extract was 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 90/10) to obtain 5-methoxy-1-(3,3-dimethylbutyl)indoline (74.6 mg, 26%).

According to the analysis of related databases, 21857-45-4, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .In analogy to intermediate 1A, 200 mg (0.87 mmol) 5-(trifluoromethoxy)-1 H-indole-2,3-dione was heated with 388 muL (4.33 mmol) 1,1,1 -trifluoroacetone, 53 mg (0.95 mmol) potassium hydroxide, 99 muL (1.73 mmol) acetic acid and 99 mg (1.21 mmol) sodium acetate in 2 mL water for 1 h at 120 C in the microwave to obtain 269 mg (0.83 mmol, 96%) of the desired title compound after aqueous work-up.1 H NMR (400 MHz, DMSO d6): delta (ppm) = 8.01 (dd, 1 H), 8.38 (s, 1 H), 8.44 (d, 1 H), 8.85 – 8.89 (m, 1 H), 14.57 (br. s. , 1 H).

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem