Month: June 2021

Electric Literature of 193354-13-1,Some common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, molecular formula is C8H6INO, 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.

3-[5-(5-Iodo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 130 mg 5-iodo-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 155 mg (71%) of the title compound as an orange solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.79 (s, br, 1H, NH-1), 8.12 (d, J=1.70 Hz, 1H, H-4), 7.65 (s, 1H, H-vinyl), 7.36 (dd, J=1.70, 7.93 Hz, 1H, H-6), 6.79 (d, J=7.93 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.27 (s, 3H, CH3); MS m/z (relative intensity, %) 437 ([M+1]+, 100).

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1201923-48-9, 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. 1201923-48-9, name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(3-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester (1.203 g, 3 mmol) and trifluoroacetic acid-dichloromethane (15 mL, 2:1) was stirred at room temperature for 1 hour and then concentrated under reduced pressure to give crude 2-[(S)-2-amino-3-(3-fluoro-phenyl)-propyl]-isoindole-1,3-dione trifluoroacetic acid salt. (Yield 1.516, 123%).

The synthetic route of (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); 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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO3

A stirred solution of 5-methoxyisatin (0.1 mol) in hydrazine hydrate (60 ml) was heated to 140C for 4 h. The reaction mixture was cooled to room temperature, poured into 300 ml of ice water, and acidified to pH 2 with 10% hydrochloric acid. After standing at room temperature for one night the precipitate was collected by vacuum filtration, washed with water, and dried under vacuum (35% yield).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1168150-46-6, 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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N-methyl-2-(4-methylpiperazin-1-yl)-N-(5-aminopyridin-2-yl)acetamide (205mg, 0.78mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindole-6-carboxylate (200mg, 0.65mmol) placed in 15mL of methanol was heated to 70 C, 13h of holding, and then cooled to room temperature, concentrate.The residue was purified by silica gel column (ethyl acetate / petroleum ether = 1/5 to 4/1) to give a yellow oil was isolated, after recrystallization (ethyl acetate / petroleum ether = 1/8) to give a bright yellow solid, methyl (Z)-(((6-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)pyridin-3-yl)amino(phenyl)methylene))-2-oxoindole-6-carboxylate (120mg, 34%).

The synthetic route of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-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.

Stage A: 1-Methyl-2-Indolinethione 148 g (1.76 mol) of sodium bicarbonate are added in 20-gram portions with brisk stirring and at room temperature to a suspension of 130 g (0.8 mol) of 1-methyl-2-indolinone, prepared according to R. A. ABRAMOVITCH and D. H. HEY (J. Chem. Soc., 1954, 1699) and 133 g (0.3 mol) of phosphorus pentasulfide in 1.30 1 of anhydrous tetrahydrofuran. After 10 hours’ stirring at room temperature, the mixture is filtered and the filtrate is concentrated on a water bath under vacuum. The residue is taken up with a water/ice mixture and the resulting mixture is extracted three times with chloroform. The organic phase is washed with water and then with saturated aqueous sodium chloride solution, dried and evaporated to dryness. The residue is recrystallized in methanol. Yield: 93%. Melting point: 177-118 C. Analysis: Calculated: C: 66.22, N: 8.58, S: 19.64. Found: C: 66.62, N: 8.63, S: 19.76.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adir et Compagnie; US5030646; (1991); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

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, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 480-91-1, name is Isoindolin-1-one, 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 480-91-1, Quality Control of Isoindolin-1-one

Intermediate 6-1Preparation of 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110 C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) delta 7.86-8.06 (2H, m), 7.41-7.71 (4H, m), 5.04 (2H, s). Mass spectrum m/z 354.9 (M+H)+.

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, Isoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., Computed Properties of C10H9Cl2NO

Example 3 Preparation of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one (Ziprasidone base) In a round bottom flask 1 g of 6-Chloro-5-(2-Chloroethyl)-1,3-Dihydro-2H-Indol-2-One (INT 1), 1.1 g of (3-(1-piperazinyl)1,2-benzisothiazole), 1.46 g of Na2CO3 and 8 ml of 1-ethyl-3-methylimidazolium methyl sulfate were placed, heated to 100 C and stirred for 24 hours. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl)-1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC. The reaction mixture was cooled to room temperature and 30 ml of methanol was added to precipitate the product. Reaction mixture was stirred for about 1 h and filtered. An amount of 1.8 g of wet crude Ziprasidone base was obtained (Purity 88.0 % was determined by HPLC). A whole sample was further placed in a 50 ml round bottom flask with 20 ml of demineralised water and heated at the 79C for 30 minutes, filtrated and cooled to room temperature. A 2.65 g of precipitated wet Ziprasidone base was dried in a vacuum drier for 1 h at the temperature 50 C and overnight at the room temperature. An amount of 1.03 g of Ziprasidone base was obtained.

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; KRKA; EP1889844; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 mixture of isatin derivatives or acenaphthenquinone(1 mmol), barbituric acid (1 mmol), 1, 3-dicarbonyl compounds(1 mmol), SBDBSAC (0.02 g) and H2O (5 mL) was added to a in a25 mL round-bottomed flask connected to a reflux condenser, andstirred under reflux conditions. After completion of the reaction, asmonitored by TLC, the reaction mixture was cooled to room temper-ature. Methanol (20 mL) was added, stirred and refluxed for 3 min.Then, the resulting mixture was centrifuged for the separation of the catalyst from the product and remaining starting materials.After the separation of catalyst from the reaction mixture, methanolwas removed and the solid residue (crude product) was trituratedby a mixture of ethanol and water (9/1) to give the pure product.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moosavi-Zare, Ahmad Reza; Zolfigol, Mohammad Ali; Noroozizadeh, Ehsan; Moratab, Rasoul Salehi; Zarei, Mahmoud; Journal of Molecular Catalysis A: Chemical; vol. 420; (2016); p. 246 – 253;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 150544-04-0, 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 150544-04-0 as follows.

Intermediate 4b and 2,5-dimethoxytetrahydrofuran (525mul) are added to acetic acid (17mL) and heated to 110°C for 3 hours. The mixture is then cooled to room temperature, diluted with water and the pH is adjusted to 10 using 2M NaOH. The reaction mixture is extracted using ethyl acetate (4 times). The organic phase is washed with water and saturated brine solution and dried over Na2SO4. The solvent is removed under reduced pressure. The residue is dissolved again in ethyl acetate and the resulting solid particles are removed by filtration. The solvent is again removed under reduced pressure to yield the desired intermediate 4c (790mg).

According to the analysis of related databases, 150544-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem