Month: June 2021

Reference of 496-12-8, 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. 496-12-8, name is Isoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven-dried RB flask, 4-chloro-2-phenyl-1H-pyrrolo[3,2-c]pyridine 6b (250 mg, 1.09 mmol) and formaldehyde solution, 37 wt.% in H2O (0.2 mL, 2.73 mmol) were mixed in glacial acetic acid(5 mL). N-methyl piperazine (273.8 mg, 2.73 mmol, CAS 109-01-3)was added drop wise at 0C. The resulting mixture was stirred atroom temperature for 12 h. After completion of the reaction, the excess solvent was evaporated to dryness under reduced pressure.The residue was neutralized with 10% NaHCO3 solution, the solidf ormed was collected by filtration, washed with water and dried.The crude product was purified by silica gel column chromatographyto provide title compound as an off-white solid (326.3 mg,88%).

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

Reference:
Article; Jose, Gilish; Suresha Kumara, Tholappanavara H.; Sowmya, Haliwana B.V.; Sriram, Dharmarajan; Guru Row, Tayur N.; Hosamani, Amar A.; More, Sunil S.; Janardhan, Bhavya; Harish; Telkar, Sandeep; Ravikumar, Yalegara Siddappa; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 275 – 288;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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. 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H3ClFNO2

2-amino-5-fluoro-6-chlorobenzoic acid 0.01mol joined is provided with a reflux condenser, magneton, thermometer in three-necked bottle, adding toluene 15 ml, dry SOCl 2 3 ml, reflux 1h, stopping reaction, rotary evaporation under reduced pressure to remove the solvent and redundant SOCl 2. Then added to the flask 0.01moL of 5-fluoro-4-chloro Indoloquinone (5-fluoro-6-chloro Indoloquinone) and 15 ml of dichloromethane, to continue to reflux reaction 1h, cooling to room temperature, filtered, to obtain the yellow solid, washing with methanol, dichloromethane or toluene recrystallization

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; Northwest University; Huo, Baolong; Wang, Cuiling; (52 pag.)CN105330666; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-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: C10H11NO

22c. 3,3-dimethylindoline To a solution of 22b (1.0 g, 6.2 mmol) in THF at 0 C. was added LiAlH4 (1M THF solution, 13.6 mL, 2.2 eq) under nitrogen. The resulting slurry was heated at reflux for 4 h. While cooling in an ice bath, sat’d Na2SO4 was added carefully to quench the extra un-reacted LiAlH4. The solids were filtered out, and were rinsed with EtOAc. The organic was washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness to give almost pure 22c (0.82 g, yield: 89%). LC-MS ESI 148 (M+H).

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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.

Take one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) 5-hydroxyindoline, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the 5-hydroxyindoline point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

The synthetic route of 172078-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Sciences Military Medical Institute; Wang Liyun; Tong Kun; Shi Weiguo; Cheng Jingchao; Yu Zixing; Ren Fengxia; Zhou Hu; Xiong Ying; (49 pag.)CN111217776; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, Product Details of 2058-72-2

General procedure: To a solution of carboxylic acid (1.3 mmol) in dry CH3CN (3 mL), were added the isatin derivative (1.00 mmol), cyclohexyl isocyanide (1.0 mmol), and sufficiently activated 4 A MS (100 mg). The resultant mixture was stirred at 80 C for the appropriate time as specified in Table 3 and was monitored by TLC. After completion of the reaction, for compounds 4a-o, the solvent was removed under reduced pressure and the residue dissolved in dry CH2Cl2. The 4 A MS was recovered by simple filtration and addition of n-hexane to the filtrate yielded the pure solid products. For compound 4o, the solvent was removed under reduced pressure and the residue was washed with dry CH2Cl2. The solid residue was then dissolved in EtOH, the 4 A MS was recovered by simple filtration, and the filtrate crystallized from ethanol to yield the pure product 4o in 60% yield.

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

Reference:
Article; Esmaeili, Abbas Ali; Amini Ghalandarabad, Saeid; Jannati, Saeideh; Tetrahedron Letters; vol. 54; 5; (2013); p. 406 – 408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 132898-96-5, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Application In Synthesis of 6-Bromoisatin

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 99365-40-9,Some common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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) 6-Bromo-3,3-dimethyl-l,3-dihydro-indol-2-one To a suspension of potassium tert-butylate (12.8 g, 114 mmol) in dry THF (80 ml) at 0C under an argon atmosphere was added portionwise 6-bromoindolin-2-one (5.0 g, 22.9 mmol) followed by copper(I) bromide-dimethylsulfide complex (470 mg, 2.29 mmol). Mel (6.82 g, 3.00 ml, 48.0 mmol) was added dropwise within 45 minutes, keeping temperature of the reaction mixture below 8C. The reaction mixture was warmed to room temperature and kept at this temperature for 16 hours. The reaction mixture was cooled to 0C again and saturated aqueous ammonium chloride solution was cautiously added. The mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as light yellow solid (5.17 g). MS ESI (m/z): 240.0/ 242.1 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 8.12 (m, 1H), 7.20-7.16 (m, 1H), 7.09-7.08 (m, 1H), 7.06-7.04 (m, 1H), 1.39 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); 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. 40314-06-5, name is 5-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H7NO2

Isovaleryl chloride (0.50 mL, 4.1 mmol) was added to a mixture of 4-methylphthalimide (0.78 g, 4.8 mmol), triethylamine (0.86 mL, 6.2 mmol), and acetonitrile (8.2 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with satd aq NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated. The crude material was purified by flash chromatography (SiO2, hexanes:EtOAc 4:1) to give 10 (713 mg, 2.91 mmol, 71%) as a white solid. 1H NMR (300 MHz, CDCl3): delta 7.83 (d, J=7.7Hz, 1H), 7.74 (s, 1H), 7.65 (d, J=7.6Hz, 1H), 2.90 (d, J=6.9Hz, 2H), 2.57 (s, 3H), 2.25 (septet, J=6.7Hz, 1H), and 1.03 (d, J=6.7Hz, 6H). 13C NMR (75 MHz, CDCl3): delta 171.6, 165.6, 165.5, 147.1, 136.2, 131.4, 128.5, 124.6, 124.3, 47.4, 25.0, 22.4, and 22.1. IR (neat): 2956, 1750, 1711, 1612, 1364, 1309, 1109, 1047, and 738 cm-1. HRMS: Calcd for C14H15NNaO3+ [M+Na+] requires 268.0944; found 268.0945. Mp: 180-186 C.

According to the analysis of related databases, 40314-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem