Author: Jessica.F

Reference of 141452-01-9, The chemical industry reduces the impact on the environment during synthesis 141452-01-9, name is Methyl indoline-5-carboxylate, I believe this compound will play a more active role in future production and life.

A solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol) in tetrahydrofuran (10 ml.) was cooled in an ice-water bath for 5 minutes. Sodium hydride (45.15 mg, 1.13 mmol) in tetrahydrofuran (2 ml.) was added drop wise and the reaction was allowed to stir under cooling for 20 minutes before the dropwise addition of acetyl chloride (0.08 ml_, 1.13 mmol). The reaction mixture was stirred for 30 minutes. The reaction mixture was removed from the ice-water bath and allowed to warm to ambient temperature. After 1 hour the reaction was added dropwise to a saturated NH4CI solution and extracted with ethyl acetate three times. The organics were combined, dried over anhydrous MgS04, filtered to remove the solids, and concentrated under reduced pressure to give methyl 1 -acetylindoline-5- carboxylate as an off-white solid (235 mg, 1.07 mmol, 95%). LCMS: MS m/z 220.1 [M+H]+; 1H NMR (400 MHz, DMSO) d 8.09 (d, J = 8.9 Hz, 1H), 7.79 (d, J = 7.6 Hz, 2H), 4.14 (t, J = 8.6 Hz, 2H), 3.81 (s, 3H), 3.17 (t, J = 8.6 Hz, 2H), 2.18 (s, 3H).

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, Methyl indoline-5-carboxylate, other downstream synthetic routes, hurry up and to see.

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

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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5,7-Dimethylindoline-2,3-dione

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39603-24-2.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromoisoindoline-2-carboxylate

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -780C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxyiic acid tert-butyl ester as a colourless oil.

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; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); 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 611-09-6 as follows. Quality Control of 5-Nitroindoline-2,3-dione

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]·2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2-Oxo-3-(4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrol-1-ylmethylene)-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 325.2 [M++1].

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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.

Step 1. Dimethyl (Phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3-hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6H), 4.12 (d, J=11.4 Hz, 2H), 7.76 (m, 2H), 7.87 (m, 2H).

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

Reference:
Patent; MethylGene, Inc.; US6472406; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, 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 102359-00-2 as follows.

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4, Recommanded Product: 1-Methylisatin

General procedure: To a mixture of isatin (1 equiv.) and indole (1 or 2 equiv.) in water (3 mL), CuWO4 (10 mol%) was added and the mixture was stirred at room temperature for 2 h or heated at 60 C for 2 h. After completion of the reaction (monitoring by TLC), the mixture was cooled (in the case of bis-indolyl-2-oxindoles) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the desired product which was purified by silica gel column chromatography. Elution of the column with PE:EtOAc gave the desired products (5 or 6).

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:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
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. 205383-87-5, name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C16H20N2O3

Tert-butyl 2-oxospiro[indoline-3,3?-pyrrolidine]-1?-carboxylate (1 g, 3.4 mmol) was added to a round bottom flask containing a stir bar and dissolved in acetonitrile (15 mL). Potassium carbonate (940 mg, 6.8 mmol) was added, followed by 4-bromo-1-(bromomethyl)-2-fluorobenzene (929 mg, 3.4 mmol). The mixture was stirred at room temperature overnight, and then evaporated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic layer was collected, and the water layer was extracted with an additional ethyl acetate (2×50 mL). The organic layers were combined, dried over magnesium sulfate, and evaporated to afford a colorless solid, which was used directly in the next step. To a microwave vial containing a stir bar was added tert-butyl 1-(4-bromo-2-fluorobenzyl)-2-oxospiro[indoline-3,3?-pyrrolidine]-1?-carboxylate (457 mg, 0.96 mmol), followed by 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (200 mg, 0.96 mmol), cesium carbonate (626 mg, 1.9 mmol), 1,1?-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) dichloromethane adduct (78 mg, 0.096 mmol), and the mixture was suspended in THF/water (4 mL, 1:1). The vial was sealed, and the mixture was heated to 160 C. for 10 min. The organic layer was removed, filtered through celite and evaporated to afford an oil, which was re-dissolved in excess TFA. This solution was allowed to stir at room temperature for 2 h, and then TFA was evaporated under reduced pressure. The resulting oil was used directly in the next step. 1-(2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)benzyl)spiro[indoline-3,3?-pyrrolidin]-2-one (75 mg, 0.2 mmol) was added to a vial containing a stir bar and dissolved in DMF (1 mL). Potassium carbonate (41 mg, 0.3 mmol) was added, followed by iodomethane (15 muL, 0.2 mmol). The vial was sealed, and the mixture was stirred at room temperature for 2 h. The suspension was filtered to remove solids, and then purified using an SCX cartridge to afford the title compound as a clear oil. LCMS: RT=0.59 min, >99% (at) 254 nm, >99% (at) 215 nm; m/z (M+1)+=391. 1H NMR (400 MHz, CDCl3, delta (ppm)): 7.7 (s, 1H), 7.6 (s, 1H), 7.5 (dd, J=7.4, 0.6 Hz, 1H), 7.3-7.1 (m, 4H), 7.1-7.0 (m, 1H), 6.8 (d, J=7.8 Hz, 1H), 5.0 (s, 2H), 4.0 (s, 3H), 3.1-3.0 (m, 1H), 3.0-2.9 (m, 2H), 2.8-2.7 (m, 1H), 2.5 (s, 3H), 2.5-2.4 (m, 1H), 2.1 (dt, J=12.8, 7.7 Hz, 1H), HRMS calculated for C23H24N4OF (M+H)+ m/z: 391.1934, measured: 391.1933.

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; VANDERBILT UNIVERSITY; Lindsley, Craig W.; Conn, P. Jeffrey; Wood, Michael R.; Hopkins, Corey R.; Melancon, Bruce J.; Poslusney, Michael S.; US2013/123236; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 100510-64-3, These common heterocyclic compound, 100510-64-3, name is 3,3-Dimethyl-6-nitroindolin-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.

A. 6-amino-3,3-dimethylindolin-2-one A mixture of 3,3-dimethyl-6-nitroindolin-2-one (1.2 g, 5.8 mmol) (Mertens et al, J. Med. Chem. 30:1279, 1987), 10% Pd-C (100 mg), and MeOH (100 mL) was stirred under hydrogen atmosphere (1 atm) for 10 h. The catalyst was filtered out and the filtrate was concentrated. The residue was purified by column to give an off-white solid (700 mg). MS: M+H=177. 1H NMR (d6-DMSO): 10.01 (s, 1H), 6.84 (d, 1H, J=8.0 Hz), 6.13-6.10 (m, 2H), 5.01 (s, 2H), 1.15 (s, 6H).

Statistics shows that 3,3-Dimethyl-6-nitroindolin-2-one is playing an increasingly important role. we look forward to future research findings about 100510-64-3.

Reference:
Patent; Kelly, Michael G.; Kincaid, John; Kaub, Carl J.; US2006/258689; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem