Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 893620-44-5, name is 6-Bromo-5-fluoroindolin-2-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 893620-44-5, COA of Formula: C8H5BrFNO

d) 6-Bromo-5-fluoro-1 ,3-trimethylindolin-2-one To a suspension of NaH (5.04 g, 126 mmol) in tetrahydrofuran (105 ml) under an argon atmosphere was added 6-bromo-5-fluoroindolin-2-one (7.24 g, 31.5 mmol) in portions. After gas evolution has ceased methyl iodide (17.9 g, 7.88 ml, 126 mmol) was added dropwise within 50 minutes by means of a syringe pump (exothermic reaction), keeping the temperature of the reaction mixture between 24C and 26C. The reaction mixture was kept at room temperature for 4 hours and then carefully quenched with aqueous ammonium chloride solution. The reaction mixture was diluted with tert-butyl methyl ether, water and saturated aqueous ammonium chloride solution. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with saturated aqueous ammonium chloride and dried over sodium sulfate. The solvent was evaporated and the residue was triturated with heptane to give the title compound as light brown solid (7.87 g). 1H NMR (CDC13, 400 MHz): (ppm) = 7.02-6.97 (m, 2H), 3.19 (s, 3H), 1.36 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-5-fluoroindolin-2-one, and friends who are interested can also refer to it.

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;,
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Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, 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 1074-82-4 as follows.

To a solution of 1 -bromo-4-bromomethyl-benzene (3.0 g, 12.0 mmol, 1.0 eq) in DMF (40 mL) was added phthalimide potassium (4.4 g, 24.0 mmol, 2.0 eq). The reaction mixture was stirred for 1 h at rt Water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2S04 and evaporated to give 2-(4-bromo-benzyl)-isoindole-l,3-dione which was used as a white solid (4.0 g, quant)without further purification.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); 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 118289-55-7 as follows. Recommanded Product: 118289-55-7

88.7 g (0.837 mols, 3.21 molar equivalents) of sodium carbonate, 600 mL of acetonitrile and 66.7 g (0.261 mols, 1.0 molar equivalent) of 3- (1-piperazinyl) -1, 2- benzisothiazole hydrochloride are added into a beaker equipped with a magnetic stirrer. The resulting white suspension is stirred for 10 minutes. At this point 60.0 g (0.261 mols, 1.0 molar equivalent) of 5- (2- chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one and 0.3 g (0.002 mols, 0.008 molar equivalents) of NaI are added. The resulting brown suspension is charged into a 1 L reactor vessel, which is purged with nitrogen and heated to 120-125 C (internal pressure increases to 400- 500 kPa) for 25 hours. The reaction is cooled to room temperature, stirred for 30 minutes, filtered and the solid washed with acetonitrile. A wet mixture of zipradisone and inorganic salts is obtained, that is further washed with acetonitrile. The resulting wet mixture of ziprasidone and inorganic salts is stirred with 675 ml of water at reflux temperature for 1 h to remove inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 140 g of wet solid (corresponding to 87 g of dry material) are obtained. EPO The wet solid is stirred again with water at reflux temperature for 1 h to remove residual inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 170 g of wet solid (corresponding to 81 g of dry- material) are obtained. HPLC analysis reveals a purity of 97.8%.To remove starting materials present in the wet solid obtained in the previous step, it is stirred twice with400 ml of tetrahydrofuran at reflux temperature. The solution is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed twice with 40 ml of tetrahydrofuran, and 60 g of wet solid, corresponding to 54.8 g of dry material, are obtained.The solid obtained is ziprasidone base having a purity of 99.4% by HPLC and the global yield from the starting compounds is 51% (molar yield) . Potentiometric titration with HClO4: 100.03%

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDICHEM, S.A.; WO2006/34965; (2006); A1;,
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, Computed Properties of C8H4BrNO2

A mixture of 6-bromoisatin (226 mg, 1 mmol), malonic acid, (114 mg, 1.1 mmols) and sodium acetate (103 mg, 1.25 mmols) and acetic acid (2.5 ml) the was stirred under a nitrogen atmosphere for 5 h. Additional sodium acetate (100 mg) was added and the resultant mixture was heated overnight. The reaction mixture was cooled to room temperature, excess acetic acid was removed under reduced pressure and the resultant pinkish brown solid was washed with copious amounts of water and dried under vacuum to obtain the desired product (234 mg, 88%). ‘H NMR (300 MHZ, DMSO-d6): 6. 88 (s, 1H), 7.44 (d, 1H), 7.58 (s, 1H), 8.18 (d, 1H), 12.11 (br s, 1H), INLZ 268

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; WO2004/81008; (2004); 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 4,7-Dichloroindoline-2,3-dione

with the operation of Example 1, the isatin (147mg, lmmol) to 4,7_ dichloro isatin (216mg, lmmol), reflux for 4h, the obtained orange-red solid product (IV-3) 2 – (3-amino-4, 7-dichloro-2-oxo-indol-3-yl) -3-hydroxy-1,4-naphthoquinone (300mg, 77%),

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; Zhejiang University of Technology; Song, Qingbao; Che, Fengfeng; Zhang, Peng; Shen, Tian Hua; (10 pag.)CN104030966; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-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 118289-55-7, SDS of cas: 118289-55-7

Preparation of 5-(2-(4-(l ,2-benzisothiazol-3-vD-1 -piperazinvl)ethyl)-6-chloro-1,3-dihvdro-2H-indol-2-one(Ziprasidone)In a 50 ml 3 necked round bottom flask there were placed 1 gram (4.56 mmol) of 3-piperazinylbenzo[d]isothiazole; 2.5 grams (10.86 mmol) of 6-chloro-5-(2-chloroethyl)indolin-2-one; 50 mg of potassium iodide; 1.64 grams (11.88 mmol) of potassium carbonate. The contents of the flask were heated to 90 C. The reaction was monitored by HPLC. After completion of the reaction, 50 ml of DM water was added to the reaction mixture and stirred. The product was filtered off and washed with water and dried to obtain 1.41 grams (75%) of 5-(2-(4-(l,2-benzisothiazol-3-yl)-l-piperazinyl)ethyl)-6-chloro-l,3-dihydro-2H-indol-2-one. The crude product was purified by IPA and/ or THF. The product matched the spectra of a standard NMR and showed the correct retention time by HPLC with 98.0% assay. The melting point of the compound was found to be 218 C-220 C, and was found to conform with the melting point of 218 C -220 C as disclosed in US. 5,206,366.

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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LUPIN LIMITED; WO2006/11157; (2006); A2;,
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 3484-35-3 as follows. Recommanded Product: 5-Methylindolin-2-one

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.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

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;,
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Indoline | C8H9N – PubChem

Related Products of 99365-40-9, These common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-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.

Four microwave vials were loaded as follows: 6-Bromoindolin-2-one (500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol), potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)Cl2*CH2Cl2 (96.0 mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 C overnight. The content of the four vials was then combined, concentrated and purified by column chromatography (cyclohexane/EtOAc) to afford the title compound as a white solid (2.27 g, 75%, purity 80%). 1 H NMR (500 MHz, CDCl3) ppm = 8.57 (bs, 1 H), 7.48 (d, J=7.3, 1 H), 7.31 (s, 1 H), 7.23 (d, J=7.3, 1 H), 3.55 (s, 2H), 1.33 (s, 12H). LC – MS (ESI, m/z) Rt = 2.75 min – 260 (M+H)+ (HPLC method B).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, kai; STIEBER, Frank; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; WO2014/63778; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

7-Benzyl-4-chloro-2-methyl-5H-pyrrolo[3,2-d]pyrimidine 11 15(0.1 g, 0.39 mmol) and 5-methoxyindoline (58 mg, 0.48 mmol) were dissolved in isopropanol (15 mL) and heated at reflux for 12 h, and the solvent was evaporated in vacuo. The crude material obtained was purified by column chromatography and eluted with 1% (v/v) MeOH/CHCl3. Fractions containing the product (TLC) were pooled, and the solvent was evaporated to afford 4 (109 mg, 76%). TLC Rf 0.4 (MeOH: CHCl3; 1:20).

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; Pavana, Roheeth Kumar; Choudhary, Shruti; Bastian, Anja; Ihnat, Michael A.; Bai, Ruoli; Hamel, Ernest; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 545 – 556;,
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Indoline | C8H9N – PubChem

132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. HPLC of Formula: C8H4ClNO4S

To a stirred solution of 19b (0.15 g, 0.5 mmol) in dry DCM (4 mL) cooled in an ice bath was added TFA (0.6 mL, 10 mmol). After 1 h bulk solvent was removed in vacuo and the residue remaining taken up in dry DCM (8 mL) and cooled in an ice bath. Dry triethylamine (1.5 mL) was then added followed by 5-chlorosulfonylisatin8(0.16 g, 0.65 mmol) in dry THF (4 mL) and the solution was then stirred. After 19 h bulk solvent was removed in vacuo and redissolved in DCM (10 mL), washed with water (2×10 mL), then brine (1×10 mL) and dried over Na2SO4. Chromatography (hexanes/ethyl acetate) gave the desired product as an orange solid (104 mg, 51%).

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; HAMMERSMITH IMANET LIMITED; ABOAGYE, ERIC OFORI; SMITH, GRAHAM; NGUYEN, QUANG-DE; ARSTAD, ERIK; GLASER, MATTHIAS EBERHARD; (78 pag.)JP5667056; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem