Category: indolines-derivatives

These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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. Formula: C8H4N2O4

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) S 7.69 (brs, 1H, NHH), 7.74 (t, J= 8 Hz, 1H, Ar), 7.92 (dd, J= 1, 8 Hz, 1H, Ar), 8.13 (dd, J= 1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH);13C NMR (DMSO-d6) S 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; TROTTER, Matthew William, Burnell; RISUENO-PEREZ, Alberto; POURDEHNAD, Michael; GANDHI, Anita; HAGNER, Patrick; (85 pag.)WO2017/53555; (2017); A1;,
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Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 20 ml pressure tube were mixed 5-nitroindoline (500 mg, 3.05 mmol) and sodium carbonate (968 mg, 9.14 mmol) at ambient temperature in anhydrous tetrahydrofuran (5 ml). Methyl iodide (0.190 ml, 3.05 mmol) was added. The reaction mixture was stirred and heated for 24 hours at 60 C. the mixture was diluted with ethyl acetate and water, and the layers were separated. The organic layer was washed with brine, dried with Na2S04, filtered, and concentrated. The residue was purified by flash chromatography on a 40 g silica gel column using an AnaLogix IntelliFlash 280 system eluting with a gradient of 10 to 20% ethyl acetate/hexane to provide the title compound. MS (DCI(+)) m/e 179 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; BA-MAUNG, Nwe Y.; CLARK, Richard F.; ERICKSON, Scott A.; FIDANZE, Steve D.; KAWAI, Megumi; MANTEI, Robert A.; SHEPPARD, George S.; SORENSON, Bryan K.; WANG, Gary T.; WO2011/53476; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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 99365-40-9, Recommanded Product: 6-Bromoindolin-2-one

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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Synthetic Route of 20870-78-4, 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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-Bromo-1,3-dihydro-indol-2-one (10 g, 47.1 mmol) in dioxane (120 ml) was added bispinacolato diborane (26.25 gm, 103.7 mmol); the reaction was purged with nitrogen for 30 min followed by addition of potassium acetate (13.86 g, 141 mmol) and Pd(dppf)Cl2 (1.92 g 2.3 mmol). The reaction mixture was warmed to 100 C. and stirred at this temperature for 16 h. After the completion of the reaction it was filtered through Celite and the filtrate was diluted with water, extracted with EtOAc. The combine organic layer ware washed with brine, dried over Na2SO4, concentrated and purified by column chromatography to obtain 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one, (7.8 g, 64%).

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

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
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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. 20870-78-4, name is 5-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromoindolin-2-one

EXAMPLE 58A 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Under N2, 5-Bromoindolin-2-one (Aldrich, 2.11 g, 10.0 mmol) was coupled with bis(pinacolato)dibon (Frontier Scientific, 3.05 g, 12 mmol) in the presence of KOAc (Aldrich, 1.50 g, 15.0 mmol) under the catalysis of PdCl2(dppf).CH2Cl2 (Aldrich, 163 mg, 0.2 mmol) in anhydrous dioxane (Aldrich, 50 mL) at 85 C. for 15 hours. After the reaction was completed, it was cooled down to ambient temperature and diluted with EtOAc (100 mL). The mixture was then washed with brine (2*10 mL) and concentrated. The residue was purified with chromatography on silica gel (EtOAc/hexanes, v. 1:1, Rf=0.5) to provide the title compound (2.43 g, yield, 93.8%). 1H NMR (300 MHz, CD3OD) delta 1.24 (s, 12H), 3.51 (s, 2H), 6.88 (d, J=8.5 Hz, 1H), 7.52-7.75 (m, 2H) ppm. MS (DCI/NH3): m/z 260 (M+H)+.

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
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2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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. SDS of cas: 2436-29-5

Bromine (0.22 ml, 4.29 mmol) was added dropwise to a solution (30 ml) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal (866 mg, 4.36 mmol) in acetic acid at room temperature. After stirring at room temperature for 2 hours, the reaction solution changed in color from brown to colorless. Thiourea (373 mg, 4.90 mmol) was added to the reaction solution and the resulting mixture was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with methanol-diethyl ether and then dried. The solvent was distilled off under reduced pressure to obtain the title compound (616 mg, 55.8%).; LC/MS (M+1, retention time): 260.0, 3.76 min.

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

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1640369; (2006); A1;,
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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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6-Bromo-7-fluoroindoline-2,3-dione

To a mixture of 6-bromo-7-fluoroindoline-2,3-dione (18.9 g, 77.5 mmol) in 2 N NaOH (350 mL) at 0 oC, H2O2 (30%, 40 mL) was added. The mixture was stirred at room temperature for 16 h. The mixture was quenched with Na2SO3, and the mixture was acidified with conc. HCl to adjust pH to 2. The precipitate was collected by filtration and dried to afford the desired product as a white solid (17 g, 94% yield).

According to the analysis of related databases, 1336963-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (335 pag.)WO2016/164675; (2016); A1;,
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39755-95-8, name is 5-Methoxyisatin, 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. COA of Formula: C9H7NO3

General procedure: To a stirring solution of indolin-2,3-dione (2.0g, 13.6 mmol, 1.0 equiv.) in anhydrous DMF, sodium hydride (60% suspension inparaffin oil, 0.65 g, 16.32 mmol, 1.2 equiv.) was slowly added at 0 oCunder inert atmosphere. After 1 h, benzyl bromide (1.78 mL, 14.96 mmol,1.1 equiv.) or prenyl bromide (1.73 mL, 14.96 mmol,1.1 equiv.) or methyl iodide ( 0.93 g, 14.96, 1.1equiv.) was added dropwise. Reaction mixture was stirred for another hour.Completion of the reaction was monitored by TLC. The reaction mixture was thenquenched with aq. NH4Cl, washed with water, extracted into ethylacetate. The ethyl acetate fraction was dried over anhydrous sodiumsulfate. It was evaporated under vacuumto give a solid compound which was purified by column chromatography on silicagel (60-120 mesh) using ethyl acetate-hexane (3:97) mixture as eluent.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gangar, Mukesh; Kashyap, Naresh; Kumar, Kapil; Goyal, Sandeep; Nair, Vipin A.; Tetrahedron Letters; vol. 56; 51; (2015); p. 7074 – 7081;,
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Some common heterocyclic compound, 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, molecular formula is C16H17NO6, 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: 88150-75-8

(B.) From ethyl 4-[2-(phthalimido)ethoxy]acetoacetate STR54 Ethyl 4-[2-(phthalimido)ethoxy]acetoacetate (200 g) was dissolved in isopropanol (1000 ml) and to this was added 2-chlorobenzaldehyde (88.1 g) and methyl 3-aminocrotonate (72.2 g). The mixture was refluxed for 21 hours then the methanol was evaporated to leave an oil which was dissolved in acetic acid (1000 ml). After granulating overnight, the precipitate was collected, washed with acetic acid then slurried in methanol (300 ml). Filtration gave the title compound the n.m.r. and ir of which were identical with those of the material prepared by part (A) above.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 88150-75-8, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); A;,
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Reference of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.N-((1-Benzylpiperidin-4-yl)methyl)-2-Oxoindoline-5-carboxamide (8i). 2-Oxoindoline-5-carboxylic acid(140 mg, 0.79 mmol), (1-Benzylpiperidin-4-yl)methanamine (135 mg, 0.66 mmol), PyBOP (412 mg,0.79 mmol), DIPEA(128 mg, 0.99 mmol), DMF (6 mL). White solid, m.p.:155-156 C, yield: 56%, 1HNMR (400 MHz, CD3OD) delta 7.73-7.68 (m, 2H), 7.53-7.42 (m, 5H), 6.91 (d, J = 8.1 Hz, 1H), 4.26 (s, 2H),3.44 (d, J = 12.5 Hz, 2H), 3.31 (s, 1H), 2.98 (t, J = 12.9 Hz, 2H), 1.97 (d, J = 13.6 Hz, 3H), 1.54 (q, J = 13.1,12.1 Hz, 2H). 13C NMR (101 MHz, CD3OD) delta 178.52, 168.90, 146.69, 130.99, 129.80, 129.40, 128.99,127.92, 127.60, 125.95, 123.42, 123.40, 108.97, 60.21, 51.86, 43.82, 42.11, 34.01, 26.82. HRMS (ESI):calcd. For C22H25N3O2 [M + H]+ 364.2020, found 364.2032.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
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