Tag: M.W=200-300

Related Products of 70478-63-6, A common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

[00290] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in MeCN (5 mL) was added CS2CO3 (652 mg, 2.0 mmol). The reaction mixture was stirred at rt for 15 min then cooled to 0-5 °C. lodomethane (0.2 mL, 3.0 mmol) added dropwise and the reaction mixture was allowed to warm to rt and stirred for a further 16 h. The mixture was partitioned between EtOAc and water and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, then dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20percent EtOAc in hexanes) to afford the compound 2 (220 mg, 92percent) as a yellow solid. 1H MR (400 MHz, DMSO-i): delta 7.97 (m, 1H), 7.86 (m, 1H), 7.70 (m, 1H), 3.03 (s, 3H).

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; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 954-81-4, 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. 954-81-4 name is N-(5-Bromopentyl)phthalimide, 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.

General procedure: To a stirred suspension of phenol (12 mmol) and K2CO3 (20 mmol) in DMF (20 mL), intermediates 2a-2e (10 mmol) were added. After stirred at room temperature for 10-12 h, the mixture was quenched with water and extracted with EtOAc for three times. The combined organic phase was dried over MgSO4, filtered and concentrated to give the crude product, which was puried by chromatography on an silica gel column (EtOAc/petroleum ether as eluent) to give the products. The preparation of compounds 3a-3e was according to the method previously described [42].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Shan, Wen-Jun; Huang, Ling; Zhou, Qi; Meng, Fan-Chao; Li, Xing-Shu; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5885 – 5893;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 320734-35-8, name is 7-Bromooxindole, 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 320734-35-8, HPLC of Formula: C8H6BrNO

To a solution of 7-bromo-l ,3-dihydro-2H-indol-2-one (200 mg, 0.94 mmol) in DMF (5 mL) were added cesium carbonate (676 mg, 2.07 mmol) and iodomethane (294 mg, 2.07 mmol). The reaction mixture was stirred at ambient temperature for 18 h, then partitioned between H2O (50 mL) and EtOAc (100 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane: EtOAc – 100:0 to 85: 15, to give the title compound. MS: m/z = 254 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromooxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/31513; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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 2058-72-2, category: indolines-derivatives

A stirred brown solution of 5-bromo-1-methylindoline-2,3-dione (500 mg, 2.083 mmol) in DCM (10 ml.) was cooled down to 0C and bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml, 3.12 mmol) was slowly added into it, followed by EtOH (0.036 ml_, 0.625 mmol). The reaction mixture was allowed to warm up and stir overnight at RT. Bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml_, 3.12 mmol) was added and the mixture was stirred 8 hr at RT. The reaction was quenched with saturated aqueous Na2C03 solution and both phases were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (Cyclohexane / 0 to 50% EtOAc). The resulting solid was diluted with MeOH (2 ml_), sonicated, cooled down to 0C and filtrated off to afford the title product (183 mg, 0.698 mmol) as a beige solid. Rt = 1.07 min (UPLC- MS); 1H NMR (400 MHz, DMSO-d6) d ppm 3.17 (s, 3 H) 7.22 (d, J=8.44 Hz, 1 H) 7.84 (d, J=8.44 Hz, 1 H) 8.01 (s, 1 H).

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; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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.

Step f. Bis(pinacolato)diboron (87.5 g, 344 mmol) was added to a solution of tert-butyl 4- bromoisoindoline-2-carboxylate (85.6 g, 287 mmol) in 1,4-dioxane (850 ml), followed by potassium acetate (56.2 g, 574 mmol), and the resulting mixture was degassed with nitrogen for 15 min. Pd(dppf)Cl2 (21 g, 28.7 mmol) was added to the reaction flask and the resulting mixture was heated at 100C for 6 h. Upon completion of the reaction, as determined by LCMS, the mixture was cooled to rt and filtered through a pad of Celite, washing with EtOAc (2 chi 50 ml). The filtrate was evaporated to dryness under vacuum to give a black oily residue, which was dissolved in DCM and passed through a silica pad, eluting with DCM. The solvent was subsequently removed under vacuum to give a solid, which was triturated with hexane (200 ml) and dried under vacuum at rt to give the desired product as a white solid (88 g, 89%). LCMS (Method R): rt 3.36 min, m/z 346, 290 (-iBu), 246 (-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.62-7.54 (m, 1H), 7.48-7.41 (m, 1H), 7.33-7.25 (m, 1H), 4.70-4.62 (m, 2H), 4.60-4.53 (m, 2H), 1.49-1.43 (m, 9 H), 1.33-1.27 (m, 12 H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-90-0, These common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

Statistics shows that 5-Bromo-1-methyl-2-oxoindoline is playing an increasingly important role. we look forward to future research findings about 20870-90-0.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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.

To a solution of 2-benzylthiazole 1111 (3.88 g, 22.1 mmol) in dry THF (60 mL) at -78 C under N2 was added LiHMDS (1 M solution in THF, 26.5 mL, 26.5 mmol) dropwise. The mixture was stirred at -78 C for 45 min, then added to a solution of 2- (bromomethyl)isoindoline-l,3-dione (6.38 g, 26.5 mmol) in dry THF (60 mL) at -78 C under N2 and the mixture was stirred at -78 C overnight. The mixture was diluted with EtOAc (300 mL), washed with water, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Pet. ether/EtOAc = 2/1) to give the title compound (2.9 g, 39%) as a yellow solid. LCMS-C: Rt 2.23 min, m/z 335.0 [M+H]+.

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; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H11NO3

To a stirred solution of acetic anhydride (5.0 mL, 53.0 mmol) and 7.7 wt % phosphorus pentoxide in methanesulfonic acid (Eaton’s Reagent) (5.0 mL, 4.60 mmol) was added 2-(3-oxobutyl)isoindoline-l ,3-dione (1.0 g, 4.60 mmol). The reaction was heated at 70 C and for 8 h. The reaction was allowed to cool to room temperature and maintained overnight. The reaction was diluted with EtOAc, washed with ice cold water, dried (Na2S04), filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Analogix, SF40-115 g, 20 – 100% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness and triturated with 10% EtOAc in hexanes, filtered and evaporated to dryness to give 2-((2,6-dimethyl-4-oxo-4H-pyran-3- yl)methyl)isoindoline-l,3-dione (290 mg, 1.024 mmol, 22.24 % yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 7.91 – 7.74 (m, 4 H), 6.06 (s, 1 H), 4.54 (s, 2 H), 2.43 (s, 3 H), 2.22 (s, 3 H). MS(ES) [M+H]+ 284.0.

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; DONATELLI, Carla, A.; WO2014/107277; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0, Quality Control of 5-Bromo-1-methyl-2-oxoindoline

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.

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; 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

Application of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-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.

Example 25: Synthesis of dimethyl-(6-phenylaminomethyl-phthalazin-l-yl)-amine; 5-Bromo-3-hydroxy-2,3-dihydro-isoindol-l-oneA mixture of zinc powder (8.68 g, 132.7 mmol), copper (II) sulfate pentahydrate(0.11 g, 0.44 mmol) and aqueous sodium hydroxide (135 mL, 2M solution) were cooled to 0 0C. Bromophthalimide (25 g, 110.6 mmol) was added in portions over 30 minutes, maintaining the temperature at 0 0C. The reaction was stirred at 0 0C for 30 minutes, and at room temperature for 3 h. The reaction was filtered, neutralized to pH 7 with concentrated HCl, diluted with EtOH, and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the desired compound (15.75 g, 63 %) as a colourless solid.

Statistics shows that 5-Bromoisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 6941-75-9.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem