Month: May 2021

Synthetic Route of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

A solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (10 ml.) was cooled in an ice-water bath for 5 minutes. Sodium hydride (45 mg, 1.13 mmol, 1.0 equiv.) in tetrahydrofuran (2 mL) was added dropwise and the reaction was stirred for 20 minutes before the dropwise addition of iodomethane (0.07 mL, 1.13 mmol, 1.0 equiv.). The reaction mixture was stirred for 30 minutes before warming to 60 C for 24 hours. Additional sodium hydride (23 mg, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) was added followed by iodomethane (0.04 mL, 0.57 mmol, 0.5 equiv.) in tetrahydrofuran (1 mL) and the reaction was stirred for a further 24 hours at 60 C. The reaction was cooled to room temperature and added dropwise to a saturated solution of NH4CI solution and extracted with ethyl acetate three times. The organics were combined, dried over anhydrous MgS04, filtered to remove the solids, and adsorbed onto silica. Purification by column chromatography (0-70% ethyl acetate in cyclohexane) gave methyl 1 -methylindoline-5-carboxylate (61 mg, 0.32 mmol, 28%) as a white solid.

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

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 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 104618-32-8, Safety of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione

EXAMPLE 2: 3- (Phthalimido) -1 , 2 , 3-tetrahydrocarbazole[0035] 4- (Phthalimido) -cyclohexanone from Example 1 is mixed with 1000 mL AcOH. Phenylhydrazine (46 g) was added and the reaction mixture was heated to reflux. After the reaction was completed, the mixture was cooled down to room temperature and filtered. The cake was washed with AcOH and dried to give the product (102g) as a light yellow solid.

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, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIRAL QUEST, INC.; WEI, Yuan; LI, Tianqiao; CHI, Yongxiang; ZHU, Jingyang; WO2010/78250; (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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Product Details of 7477-63-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

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; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4403-36-5

To 3-exo-[(R)-1-((S)-2-methyl-propane-2-sulfinylamino)-2-(2,4,5-trifluoro-phenyl)-ethyl]-8- aza-bicyclo[3.2.1]octane (265 mg, 0.68 mmol) in dichloromethane/1M NaOH (1/1, 5 mL) is added 2-phthalimidoethane sulfonyl chloride (577 mg, 2.05 mmol) then the resulting mixture is stirred at 50C during 16h. It is extracted with dichloromethane, the organic phase is dried and evaporated to give a white solid. MS: 626 [M+H]+HPLC (Zorbax SB C18, 2min method (0-0.8min 10-95%ACN, 0.8-1.5min 95%ACN, 1.5- 1.6min 95-10%ACN, 1.6-2min 10%ACN): 1.25 min.

According to the analysis of related databases, 4403-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/115821; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 88150-75-8, The chemical industry reduces the impact on the environment during synthesis 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, I believe this compound will play a more active role in future production and life.

Orthochlorobenzaldehyde (67.5 g, 0.48 M) was reacted with ethyl 4[2-(phthalimido)ethoxy acetoacetate (100 g, 0.31 M) in the presence of pyridine acetic acid in benzene at 80/82 C. for 12 hrs and cooled to room temperature. To the reaction mass water was added. Organic layer was separated and benzene was distilled out and the residue was washed with hexane.

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, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Purohit, Arun Kumar; Desai, Brahmader Chilu; Shete, Balasaheb Dashrath; Bagwan, Salim Abbas; US2004/44218; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 59-48-3, 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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1 H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 No.18fer/-Butyl (5-bromo-l-oxo-l ,3-dihydro-2 /-isoindol-2-yl)acetate5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0 C. NaH (38 mg, 0.94 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0 C for 15 minutes before tert-butyl bromoacetate (92 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0 C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added. The mixture was extracted with EtOAc, and the organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. LRMS (ESI) calc’d for C14H16BrN03 [M+Na]+: 348, Found: 348.

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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.

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 2 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 to give 65 mg (42%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.30 (s, br, 1H, NH-1′), 12.05 (s, br, 1H, COOH), 10.67 (s, br, 1H, NH-1), 7.57 (s, 2H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1H, H-2′), 6.91 (d, J=7.82 Hz, 1H, H-6), 6.74 (d, J=7.82 Hz, 1H, H-7), 2.65 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2H, CH2CH2COOH), 2.30 (s, 3H, CH3), 2.25 (s, 3H, CH3); MS m/z (relative intensity, %), 311 ([M+1]+, 100).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

To 10 ml schlenk bottle by adding 5 – bromo -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material 5 – bromo -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product 5 – […], I – 6, the isolation yield is 76%

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

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

To A NN-DIMETHYLFORMAMIDE/ACETONITRILE, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 ML, 3 mmol) was added 2-oxoindoline-5-carboxylic acid (0.354 g, 2.0 mmol; described in: Sun L. et al. J. MED. Chem. 2000, 43 (14), 2655:), O- (BENZOTRIAZOL-1-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (0.77 g, 2.4 mmol) and 1-HYDROXYBENZOTRIAZOLE hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2- (AMINOMETHYL) pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NAHCO3 solution (10 ML). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9: 1), as the eluent : 1H NMR (DMSO-d6, 400 MHz) 8 10. 66 (s, 1 H), 8.96 (t, 7= 5. 6 HZ, 1 H), 8.55 (d, J = 4.4 Hz, 1 H), 7. 85 (d, J = 8. 0 HZ, I H), 7.83 (s, 1 H), 7. 78 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.29 (t, J= 6. 4 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 4.59 (d, J = 6.0 Hz, 2 H), 3. 58 (s, 2 H); MS (EI) MLZ 268 (M++1).

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem