Author: tianli

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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., 446292-07-5

To suspension of 2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-1H-isoindole-1,3(2H)-dione (170 gm) and potassium carbonate (59.3 gm) in dichloromethane (1500 ml) was added 1,1′-carbonylbis(1H-imidazole) (153.4 gm) at room temperature. Reaction mass was then stirred for 5 hr at room temperature. After completion of reaction, inorganic base is removed by filtration. The obtained filtrate is concentrated under reduced pressure to yield solid. To this solid tetrahydrofuran (850 ml) was added followed by stirring and filtration. The obtained solid is dried under vacuum for 4 hr at 50 C. to obtain 2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione. [Yield=160 gm (88.2%); Purity (HPLC)=99.65%]

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; Mathad, Vijayavitthal Thippannachar; Patil, Nilesh Sudhir; Niphade, Navnath Chintaman; Mali, Anil Chaturlal; Bodake, Mahendra Bhagirath; Ippar, Sharad Subhash; Talla, Rajesh; US2015/11756; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3484-35-3

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, 1 H, NH-1′), 12.05 (s, br, 1 H, COOH), 10.67 (s, br, 1 H, NH-1), 7.57 (s, 2 H, H-vinyl, H-4), 7.12 (d, J=2.65 Hz, 1 H, H-2′), 6.91 (d, J=7.82 Hz, 1 H, H-6), 6.74 (d, J=7.82 Hz, 1 H, H-7), 2.65 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.46 (t, J=6.94 Hz, 2 H, CH2CH2COOH), 2.30 (s, 3 H, CH3), 2.25 (s, 3 H, CH3); MS m/z (relative intensity, %) 311 ([M+1]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3484-35-3, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, molecular formula is C21H21N3O5, 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. 446292-07-5.

Amino alcohol 170 gm, 0.4293 moles and Triethylamine 41 14.72 gms, 0.9459 moles, was charged to Dichloromethane 2380 ml and cooled reaction mass to 0C – 5C. To the cooled reaction mass added triphosgene solution, 51.09 gms in 340 ml MDC, 0.18 moles drop wise at 5C – 10C in 60 min, and stirred for 60 – 90 min. Reaction mass quenched with water and distilled out MDC layer atmospherically till thick solid mass obtained. To the thick solid, charged tetrahydrofuran 1360 ml, distilled out 130 ml under vacuum. Cooled slurred mass to 25C -30C, stirred for 30 min, filtered. Wet material dried at 55C -60C to afford 162 gm dry material. Yield- 89%

The synthetic route of (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNICHEM LABORATORIES LTD; SATHE, Dhananjay G.; DAS, Arijit; RAIKAR, Sanjay; SURVE, Yashwant S.; PANDIT, Bhushan S.; (25 pag.)WO2018/127762; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

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 oneportion at room temperature to a stirred solution of isatinderivative 2 (1 mmol) and L-proline (3) (0.12 g, 1 mmol) inethanol (10 ml). The reaction mixture was stirred for 8 h.The solvent was then removed under reduced pressure, andthe residue was recrystallized from ethyl acetate as white powder.

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; 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

Adding a certain compound to certain chemical reactions, such as: 1914-02-9, name is 3,3-Dimethylindoline, 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 1914-02-9, 1914-02-9

To a solution of (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (141 mg, 0.745 mmol) in 7 mL DMF, triethylamine (125 mu,, 0.897 mmol) and HATU (322 mg, 0.847 mmol) were added. After stirring at room temperature for 5 min, 3,3-dimethylindoline (101 mg, 0.686 mmol) was added. After stirring at room temperature for overnight, the mixture was extracted with AcOEt and brine. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give (R)-tert-butyl (l-(3,3-dimethylindolin-l-yl)-l-oxopropan-2- yl)carbamate (205 mg) as a white solid. LCMS m/z = 319.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 1.358 (s, 3H), 1.364 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H), 1.45 (s, 9H), 3.78 (d, J = 10.0 Hz, 1H), 4.00 (d, J = 10.0 Hz, 1H), 4.54-4.61 (m, 1H), 5.46 (d, J = 8.5, 1H), 7.07-7.10 (m, 1H), 7.15-7.16 (m, 1H), 7.20-7.24 (m, 1H), 8.17 (d, J = 8.1 Hz, 1H).

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, 3,3-Dimethylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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. 2913-97-5.

A solution of the product of Example 3E (36.81 g) in methanol (50 mL) was treated with L-iso-leucine tert-butyl ester hydrochloride (30 g, 134 mmol), sodium cyanoborohydride (16.9 g, 268 mmol), and acetic acid (4.6 ml, 80.4 mmol), stirred at 25¡ã C. for 3 hours and concentrated. The concentrate was partitioned between dichloromethane and saturated NaHCO3. The organic phase phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with a gradient starting with 10percent-066percent ethyl acetate in hexanes to give the title compound (28.44 g, 59percent yield).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 603-62-3, name is 3-Nitrophthalimide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 603-62-3

3-NITROPHTHALIMIDE (LOOGR) was taken into a hydrogenation kettle and dissolved using 500ML of dimethylformamide. 5% Palladium/carbon (LOGR, 50% wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogen uptake was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80C. Water (500ml) was added to the residue and the mixture stirred for 30min. The product was isolated by filtration and dried at 60-70C to get 80GR (95%) of yellow crystalline solid of 3- aminophthalimide. Melting point: 263-4C.

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, 603-62-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 17630-75-0, name is 5-Chloro-2-oxindole, 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 17630-75-0. 17630-75-0

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

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 5-Chloro-2-oxindole.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, Name is 6-Bromoindolin-2-one, 99365-40-9, 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.

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and thiophene-3-boronic acid (4.3 g, 33.6 mmol). The mixture was stirred at 100 C. in an oil bath for 12 hours. The reaction mixture was cooled, diluted with ethyl acetate (500 mL), washed with IN hydrochloric acid (200 mL), water (200 mL), saturated sodium bicarbonate (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give a black solid. The solid was triturated with methylene chloride to give 2.02 g (36%) of 6-thiophen-3-yl-1,3-dihydroindol-2-one as a purple-gray solid. 1H NMR (360 MHz, DMSO-d6) delta 10.49 (s, 1H, NH), 7.77 (s, 1H, Ar-H), 7.59 (m, 1H, Ar-H), 7.45 (m, 1H, Ar-H), 7.24 (m, 2H, Ar-H), 7.07 (m, 1H, Ar-H), 3.46 (s, 2H, CH2CO). MS m/z: 215 [M]+.

Statistics shows that 6-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 99365-40-9.

Reference:
Patent; Sugen, Inc.; US6689806; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, 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.

EXAMPLE 4 2 moles of Piperazine Benzisothiazole , 1 mole of 5-(2-chloroethyl)-6-chlorooxindole in water (20 times based on benzisothiazole) and in the presence of dispersing agent. All the reactants are charged in to the flask and refluxed under nitrogen, under stirring for 12-16 hr. After the completion of the reaction, the reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried in water and then in IPA and isolated by filtration. The solid is dried at 95-100 C.Yield: 92%, Purity 99% (min).

According to the analysis of related databases, 6-Chloro-5-(2-chloroethyl)indolin-2-one, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALKEM LABORATORIES LIMITED; US2011/3995; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem