Month: March 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9NO3

Add 420 ml of dioxane to the flask, 33.0 g of compound 2, 25.6 gN-hydroxyethyl phthalimideAnd 55.0g sodium hydroxide,An additional 5.5 g of PEG-400 was added. The temperature was raised to reflux for 3 h, cooled to room temperature and filtered.The filtrate was concentrated under reduced pressure to nearDry, add 300ml water and stir for 1h, can not be cured.Extracted with toluene (50 ml x 3), combined with toluene, washed with water and dried.The solvent was evaporated to give a pale brown viscous liquid.Yield: 89.1%, purity: 92.5% (according to high-performance liquid chromatography peak area normalization method)meter).

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; Changzhou Ruiming Pharmaceutical Co., Ltd.; Shi Weiming; Zhou He; Wang Xiaoliang; (6 pag.)CN107935912; (2018); A;,
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 550-44-7 as follows. HPLC of Formula: C9H7NO2

(3,3? ? ,5,5? ? -tetra(trifluoromethyl)-1,1? :3?,1? ? -terphen-5? -yl)magnesium iodide was prepared from 5? -iodo-3,3? ? ,5,5? ? -tetra(trifluoromethyl)-1,1? :3? ,1? ? -terphenyl (3.49 g, 6.0 mmol) and magnesiumturnings (1.0 g) activated by 1,2-dibromoethane in diethyl ether (20 ml) at roomtemperature. The suspension of the Grignard reagent was cannulated into a solution of N-methylphthalimide (161 mg, 1.0 mmol) in toluene (10 ml) at roomtemperature. The mixture was heated in an oil bath at 120 C and concentrateduntil the volume was reduced to around 10 ml. Then, the Schlenk flask wassealed and stirred at 120 C for 1 d. After cooling to room temperature, themixture was quenched by a saturated aqueous NH4Cl solution and extracted withdichloromethane (3 ¡Á 50 ml). The combined organic phase was dried over MgSO4,filtered through a pad of Celite and evaporated to dryness, and the residue waspurified by flash silica-gel column chromatography (hexane/EtOAc = 97/3 to90/10). All fractions containing 1c were combined and evaporated to dryness.The obtained crude 1c was washed with hexane and benzene repeatedly, thendried in vacuo at 120 C overnight to afford 1c as a colourless solid (783 mg,0.37 mmol, 37% yield). 1H, 13C{1H} and 19F{1H} NMR spectra can be found inSupplementary Figs. 5-7.

According to the analysis of related databases, 550-44-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nakano, Ryo; Jazzar, Rodolphe; Bertrand, Guy; Nature Chemistry; vol. 10; 12; (2018); p. 1196 – 1200;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-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.

General procedure: A solution of POCl3 or POBr3 (30 mmol) in anhydrous DCM (7 mL) was added dropwise to DMF or DMA (30 mmol) in anhydrous DCM (15 mL) at 0 C. The mixture was stirred for 30 min at room temperature. Then, a solution of 1H-isoindolinone 1 (2 g, 15 mmol) in anhydrous DCM (75 mL) was added to the mixture, at 0 C. Subsequently, the reaction mixture was heated at reflux for 5 h, and then after cooling, the solvent was removed at reduced pressure. Ice-water was added, and the mixture was neutralized with NaOH 5 M. The precipitate was filtered out, washed with water and dried. The residue was recrystallized from MeOH/H2O (1:1) to give the following compounds.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diana, Patrizia; Martorana, Annamaria; Barraja, Paola; Montalbano, Alessandra; Carbone, Anna; Cirrincione, Girolamo; Tetrahedron; vol. 67; 11; (2011); p. 2072 – 2080;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. COA of Formula: C8H4KNO2

To a stirred solution of 1,6-dibromohexane (12.3 mL, 81.0 mmol) in DMF (10 mL), was added potassium phthalate (5.0 g, 27.0 mmol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90 C for 18 h, then quenched with water (300 mL) and extracted with diethyl ether (150 mL x 2). The combined organic extracts were washed with water (100 mL x 2), followed by brine (50 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 3-i as an off- white solid (6.3 g, 76% yield). LCMS: 310.95 (M+l).

The synthetic route of Potassium 1,3-dioxoisoindolin-2-ide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (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 7477-63-6 as follows. Quality Control of 7-Chloroisatin

General procedure: A magnetically stirred mixture of naphthalene-1-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 25 mL round bottom flask fitted with a reflux condenser and argon atmosphere and was refluxed for 5h and followed by usual work up and column chromatographyof the crude residue over silica gel (25 percent ethyl acetate in petroleum ether) toafford the pure products (5).

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 16800-68-3, These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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.

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven dried reaction vial, ligand 1d (2.5 mol%) was dissolved in dry toluene (1 mL), and to the resulting solution Ti(OiPr)4(5 mol%) was added and the resulting solution was stirred for 2 hunder N2 at RT. To the above stirred solution (Ia)/isatin (0.17 mmol) was added and the stirring was further continued for another 30 min. After that, DMP (0.19 mmol) was added dropwise to the above solution over 30 min. While in the case of isatin derived ketimines, initially ligand 1d (2.5 mol%) was dissolved in dry toluene (1 mL), and Ti(OiPr)4(5 mol%) was added to it and the resulting solution was stirred for 2 h at RT. Then 4 A MS (20 mg)and isatin derived ketimines (IVa) were added under stirring condition. After 30 min, DPP (IIb) was added over a period of 30 min.The reaction was monitored by TLC using hexane/ethyl acetate(70/30) as eluent. After the completion of the reaction, the solvent was removed on a rotary evaporator, and the product was purified by flash column chromatography on a silica gel column(eluted with hexane/ethyl acetate = 70/30). The purified products were characterized by LCMS and NMR.

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

Reference:
Article; Nazish, Mohd; Jakhar, Ajay; Khan, Noor-Ul H.; Verma, Shailesh; Kureshy, Rukhsana I.; Abdi, Sayed H.R.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 515; (2016); p. 116 – 125;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

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

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

337536-15-9, name is 4-Bromoisoindolin-1-one, 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. Safety of 4-Bromoisoindolin-1-one

Step 4: tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate To a solution of 4-bromoisoindolin-1-one (4 mmol) in THF (8 mL) was added borane-dimethyl sulfide complex (2M in THF, 14 mL) at 0 C. The reaction mixture was allowed to stir at reflux overnight and was then cooled to 0 C. The reaction mixture was quenched by the slow addition of MeOH (2 mL) and then 3N HCl. The reaction mixture was allowed to stir at reflux for 3 hr and then concentrated. Water was added to the residue and the pH of the solution was adjusted to >9 with 4N NaOH. The solution was extracted with diethyl ether. The organic solutions from this basic extraction were combined, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindoline, which was dissolved in THF (5 mL). To this solution was added potassium carbonate (4 mmol) in water (0.5 mL), and BOC2O (2 mmol). The reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.8 mmol, 20%).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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. Formula: C9H6BrNO2

General procedure: A 5 mL of two-necked flask with 25 mg of freshly activated 4A molecular sieves and micro stirbar was flame heated under vacuum and refilled with Nitrogen. Isatin derivative (0.10 mmol, in 0.5 mL of benzene, 0.5 M) was charged to the cooled round bottom under argon, followed by addition of carbamoylsilane (0.15 mmol) in 0.1 mL of benzene. The sealed reaction mixture was stirred at 60 C until no isatin derivatives could be detected by TLC. Volatiles were removed in vacuum to afford the crude product which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate combination) to give compound 3.6

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem