Author: Jessica.F

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;,
Indoline – Wikipedia,
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;,
Indoline – Wikipedia,
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

Related Products of 150560-58-0,Some common heterocyclic compound, 150560-58-0, name is 5-Isopropylindoline-2,3-dione, molecular formula is C11H11NO2, 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: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL×4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Isopropylindoline-2,3-dione, its application will become more common.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-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. Quality Control of 4,7-Dichloroindoline-2,3-dione

Example II-87: (5-Hydroxy-1H-pyrazol-3-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2-dihdyro- indol-3-ylidene]-hydrazide (06I6L (5-HYDROXY-1H-PYRAZOL-3-YL3-ACETIC acid hydrazide (56 mg, 0. 36 mmol) and the isatin (45 mg, 0.30 mmol) were suspended in absolute ethanol (-2-5 mL) in A closed vial and stirred in a 110 C oil bath for 2 days and, if needed, an additional 2 h at 150 C. The warm reaction mixture was evaporated with a stream of nitrogen to about one-fourth volume and acetic acid (-1-3 mL) was added and warmed to partially dissolve the solids. After cooling, the yellow solids were collected and washed with ethanol, and dried. This process was repeated if necessary. [0617] 1HNMR (400 MHz, D6-DMSO) o 12.60 (s, 1 H), 11.85 (s, 1 H), 11.5 (br s, 1 H), 9.5 (br s, 1 H), 7.44 (d, 1 H), 7.16 (d, 1 H), 5.40 (s, 1H), 4.0 (br s, 2H); LCMS-APCI m/z 354 [M+1] +.

The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, INC.; WO2005/5378; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil. Rf = 0.32 (silica gel, hexane/EtOAc = 1/1); 1H NMR (300 MHz, CDCl3) delta 7.83 (d, J = 6.6 Hz, 1H, ArH), 7.56-7.41 (m, 3H, ArH), 5.70 (ddt, J = 6.3, 10.5, 17.1 Hz, 1H, CH),4.97-4.90 (m, 2H, CH2), 4.53 (t, J = 4.2 Hz, 1H, CH), 3.11 (s, 3H, CH3), 2.13-2.00 (m, 2H, CH2), 1.80 (m, 1H,CH2), 1.60 (m, 2H, CH2); 13C NMR (75 MHz, CDCl3) delta 168.5 (C), 144.6 (C), 137.1 (CH), 132.7 (C),131.2 (CH), 128.0 (CH), 123.4 (CH), 121.9 (CH), 115.1 (CH2), 60.9 (CH), 29.7 (CH2), 27.2 (CH3),26.6 (CH2).

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

Reference:
Article; Sengoku, Tetsuya; Nagai, Yuichiro; Inuzuka, Toshiyasu; Yoda, Hidemi; Synlett; vol. 30; 2; (2019); p. 199 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem