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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., COA of Formula: C8H4FNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The reaction condition is three: under the protection of nitrogen, the 6 – bromo indole -2 – ketone (212.0 mg, 1.0 mmol), potassium carbonate (276 mg, 2 mmol), tetrabutyl ammonium bromide (33 mg, 0.1 mmol) is placed in the dual-port reaction bottle. The good sealing of the reaction device, replacing the nitrogen three times, nitrogen balloon is inserted. Injection 22 ml tetrahydrofuran, in 85 C under stirring conditions for 30 min, then slowly injected into the 3 ml bromo hexane, maintain 85 C under stirring 8 h. To be reaction slowly cooling to the room temperature after quenching in the into ice water, dichloromethane is used for extracting the organic phase, deionized water after washing three times, the organic phase for water-free magnesium sulfate drying. After filtering the organic phase by the vacuum concentrated under reduced pressure to get the crude product, using column chromatography (eluate to DCM/PE=1:1) purification, to obtain white waxy solid compound 1 – hexyl -6 – bromo – indolone (172 mg), yield 58.1%.

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Lai Wenyong; Meng Cheng; Li Xiangchun; Huang Wei; (19 pag.)CN108794494; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: (2E,2’E)-3,3′-Benzene-1,4-diylbis(1-phenylprop-2-en-1-one) (1) (0.34 g, 1 mmol) was added in one portion at room temperature to a stirred solution of isatin 2(1 mmol) and sarcosine (4) (0.09 g, 1 mmol) in 10 ml ethanol. The reaction mixture was stirred for 8 h. The solvent was then removed under reduced pressure, and theresidue was recrystallized from ethyl acetate as white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Keshipour, Sajjad; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 467 – 471; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 467 – 471,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 20780-72-7, name is 4-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H4BrNO2

General procedure: Isatin 1 (1 mmol), active methylene 2 (1 mmol), phosphite 3 (1mmol), and [DABCO-H][AcO] (17.2 mg, 0.1 mmol) were added to THF(0.3 mL). Then the reaction mixture was vigorously stirred at r.t. Theprogress of the reaction was monitored by TLC (n-hexane?EtOAc,4:1). After completion of the reaction, cold H2O (2 mL) was added. TheIL catalyst dissolved in the H2O and the insoluble crude products wereisolated by simple filtration. The crude products were recrystallizedfrom EtOH to afford pure final products. After removal of the H2O underreduced pressure, the catalyst [DABCO-H][AcO] could be directlyreused for the next run under similar reaction conditions.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Lan-Lan; Yang, Cheng; Yu, Ya-Qin; Xu, Da-Zhen; Synthesis; vol. 49; 7; (2017); p. 1641 – 1647;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 19155-24-9 name is 3,3-Dimethylindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 1 5-amino-l-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et.al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of cone, sulfuric acid using mechanical stirring and cooled using a -40 C cooling bath until stirring became difficult. A solution of 10.1 ml of fuming nitric acid and 50 ml of cone, sulfuric acid was added dropwise and the reaction allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 3Ig).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dimethylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; WO2007/120339; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

110568-64-4, name is 6-Nitroisoindolin-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. HPLC of Formula: C8H6N2O3

Intermediate 6[00204] A suspension of Intermediate 6B (1.6 g, 8.98 mmol) and Pd/C (0.18 g) in MeOH (100 mL) was stirred under H2 (1 atm) for 4 h. The reaction mixture was filtered and the filter cake was washed with MeOH. The combined filtrates were concentrated in vacuo. The crude solid was triturated with MeOH (10 mL) and dried in vacuo to yield Intermediate 6 (800 mg, 5.40 mmol, 60.1 % yield) as a beige solid. 1H NMR (400 MHz, DMSOd6) delta ppm 4.15 (s, 2 H) 5.26 (s, 2 H) 6.77 (dd, J=8.25,2.20 Hz, 1 H) 6.80 (s, 1 H) 7.16 (d, J=8.79 Hz, 1 H) 8.29 (s, 1 H). MS (ESI) m/z 149.2 (M+H)+.

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); 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 100510-64-3 as follows. Formula: C10H10N2O3

B. 6-Amino-3,3-dimethylindolin-2-one A mixture of 3,3-dimethyl-6-nitroindolin-2-one (500 mg, 2.4 mmol), 10% Pd-C (100 mg), and MeOH (100 mL) was stirred under H2 (1 atm) for 3 h. After that the catalyst was filtered off and the filtrate was concentrated to give an off-white solid (420 mg). MS: M+H=177.3

According to the analysis of related databases, 100510-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kelly, Michael G.; Janagani, Satyanarayana; Wu, Guoxian; Kincaid, John; Lonergan, David; Fang, YunFeng; Wei, Zhi-Liang; US2005/277643; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 150560-58-0, 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. 150560-58-0, name is 5-Isopropylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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¡Á4). 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.

The synthetic route of 5-Isopropylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

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

Reference of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

Intermediate 60 : 2-(3-(3-Oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (0587) A mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (499.4 mg, 2.458 mmol, commercially available from Fluorochem), piperazin-2-one (376.1 mg, 3.76 mmol, commercially available from Sigma Aldrich) and Na(0Ac)3BH (779.9 mg, 3.68 mmol) in 2-MeTHF (20 mL) was stirred at rt for 21 h 40 min. Further Na(OAc)3BH (516.6 mg, 2.437 mmol) was added after 3 h. AcOH (0.014 mL, 0.246 mmol) was added after 4 h 45 min. After 20 h 40 min further 2-MeTHF (5 mL) was added and the reaction mixture was heated to 60 C. Further Na(OAc)3BH (279.9 mg, 1.321 mmol) was added after 3 h 20 min at 60 C. Further Na(OAc)3BH (496.8 mg, 2.344 mmol) was added after 25 h 45 min at 60 C. The mixture was removed from heating and stirring after a total of 31 h at 60 C and cooled to rt. To this mixture was added sat. NaHCCte (2 mL) and water (8 mL). The mixture was stirred at rt for 20 min and extracted with EtOAc (3 x 10 mL). The organic layer was filtered through a cartridge fitted with a hydrophobic frit and the volatiles evaporated in vacuoto give an oil which was redissolved in MeOH (approx. 5 mL) and applied to the top of a 20 g Isolute aminopropyl ion exchange column. The column was eluted with 4 column volumes of MeOH and 4 column volumes of aqueous 2M HCI. The second MeOH fraction was evaporated in vacuoto give a pale yellow solid; 2-(3-(3-oxopiperazin- l-yl)propyl)isoindoline-l,3-dione (595.1 mg, 2.071 mmol, 84 % yield). (0588) LCMS (2 min high pH); Rt = 0.71 min, m/z = 288 for [MH]+

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); 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 14192-26-8 as follows. category: indolines-derivatives

Intermediate Ia (4Og) is dissolved in methanol (40OmL) and IM NaOH solution (420 mL) is added. The mixture is heated under reflux for 3 hours. The reaction is then neutralized with IM HCl. The methanol is then removed under reduced pressure and water is added EPO until precipitation commenced. The precipitate is collected via filtration, washed with water and dried under reduced pressure to yield the desired intermediate 2a (37g)

According to the analysis of related databases, 14192-26-8, 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