Tag: M.W=100-200

39755-95-8, Name is 5-Methoxyisatin, 39755-95-8, 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.

5-Methoxyisatin (2.00 g, 11.2 mmol) was dissolved into 47% hydrobromic acid (20 mL) and refluxed at 150 C for 3 h. The solution was diluted with water (100 mL) and extracted by ethyl acetate (300 mL ¡Á 5). The organic layers were combined and dried with anhydrous sodium sulfate. After concentration in vacuo, the crude dark-brown solid (1.64 g, 89% yield) was obtained. In the subsequent synthesis, 5-hydroxyisatin was used without further purification. 1H NMR (CD3OD, 500MHz) delta 6.78 (d, 1H, J=8.3Hz, H-7), 6.94 (d, 1H, J=2.4Hz, H-4), 7.02 (dd, 1H, J=8.3, 2.4Hz, H-6).

Statistics shows that 5-Methoxyisatin is playing an increasingly important role. we look forward to future research findings about 39755-95-8.

Reference:
Article; Yasuda, Daisuke; Takahashi, Kyoko; Ohe, Tomoyuki; Nakamura, Shigeo; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7709 – 7714;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, molecular formula is C9H7NO3, 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. 118-29-6.

A mixture of phthalimide (41.14 g, 0.30 mol) and distilled water (100 mL) was stirred for 10 min at room temperature. After addition of formaldehyde solution (40%, 27 mL, 0.36 mol), the resulting solution was refluxed for 1.5 h. After cooling to 0-5 C, the resulting precipitate was collected by filtration, washed with cold water (0-5 C, 200 mL) and dried in air to give the corresponding N-hydroxymethylphthalimide (51.01 g, 96% yield).(0010)A solution of thionyl chloride (23.0 mL, 37.7 g, 0.32 mol) in dichloromethane (50 mL) was slowly added to a mixture of the resulting N-hydroxymethylphthalimide and dichloromethane (550 mL) and N,N-dimethylformamide (350 mL) during 30 min at room temperature with stirring. The resulting mixture was further stirred for 2 h at room temperature. After cooling to 0 C, water (200 mL) was added slowly. And the solution was neutralized to pH 6.7-7.0 by using saturated aqueous NaHCO3 solution. The organic layer was separated and then was dried over anhydrous magnesium sulfate. After evaporation of the solvent under the reduced pressure, the residue was washed with n-hexane (100 mL) to give N-chloromethylphthalimide (51.4 g, 93% yield).(0011) N-Chloromethylphthalimide (51.0 g, 0.26 mol) was dissolved in acetone (500 mL) and potassium O-ethyl xanthate (43.9 g, 274 mmol) was added portionwise in an ice water bath under stirring. The resulting solution was further stirred for 10 h at room temperature. After removal of the solvent, the residue was dissolved in dichloromethane. The resulting solution was washed with water and dried over sodium sulfate. After removal of the solvent under the reduced pressure, pale yellow solid was obtained and recrystallized from ethyl acetate to afford the xanthate 1 as colorless crystals 67.2 g, 92% yield, mp: 99-100 C. Lit.20 mp: 94-95 C. 1H NMR (CDCl3, 400 MHz) (delta, ppm) 1.47 (t, J=7.1 Hz, 3H, CH3), 4.68 (q, J=7.1 Hz, 2H, CH2), 5.34 (s, 2H, CH2), 7.75 (dd, J=5.5, 3.1 Hz, 2H, ArH), 7.88 (dd, J=5.5, 3.1 Hz, 2H, ArH). 13C NMR (CDCl3, 100 MHz) (delta, ppm) 13.7, 41.2, 70.5, 123.6, 131.8, 134.4, 166.6, 210.2.

The synthetic route of 2-(Hydroxymethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 3; (2013); p. 1050 – 1056;,
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1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. 1074-82-4

General procedure: The appropriate dibromoalkane derivative 2a-2e (11.9 mmol) was added slowly to a mixture of the starting material phthalimide potassium salt (1) (1g, 5.4 mmol) and anhydrous K2CO3 (0.82 g, 5.94 mmol) in acetone (15 mL). The reaction mixture was heated to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (50 mL) was added to the residue and the mixture was extracted with dichloromethane (30 mL ¡Á 3). The combined organic phases were washed with saturated aqueous NaCl, dried over Na2SO4, and filtered. The solvent was evaporated to dryness under reduced pressure. The crude product was purified on a silica gel chromatography using dichloromethane/acetone (50:1) as eluent to give the intermediates 3a-3e.

Statistics shows that 1074-82-4 is playing an increasingly important role. we look forward to future research findings about Potassium 1,3-dioxoisoindolin-2-ide.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., 1074-82-4

To a solution of l-bromopropan-2-one (5 g, 36.5 mmol, 1.0 equiv) in ACN (50 mL) was added potassium l,3-dioxoisoindolin-2-ide (7.5 g, 40.5 mmol, 1.11 equiv.). The mixture was stirred at 80 C for 2 h, cooled to rt, and quenched with water (50 mL), and extracted with DCM (50 mL) twice. The combined organic layer was washed with brine (100 mL), dried over Na2S04, concentrated under reduced pressure, and purified by silica gel column chromatography using PE/EA (1/2) as eluent to afford 6.6 g of 2-(2- oxopropyl)isoindoline-l,3-dione (Intermediate 64-1) as a yellow solid. LRMS (ES) m/z 204 (M+H).

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Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
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324-03-8, 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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one (10 g, 38.6 mmol) was added in toluene (250 ml_). The mixture was cooled down to 0C and NaH 60% in mineral oil (2.315 g, 57.9 mmol) was added portionwise. The reaction mixture was allowed to warm up and stir at RT for 30 min. Dimethyl sulfate (5.53 ml_, 57.9 mmol) was added and the reaction mixture was heated up and stirred at 60C for 3 hr, cooled down to 5C and quenched with water (50 ml_). The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHC03 solution and brine. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure to afford the title product (1 1.3 g, 36.0 mmol, 93% yield) as brown solid. Rt = 1.03 min (UPLC-MS); ESI-MS = 274.2 [M+1]+ (UPLC-MS); 1H NMR (400 MHz, DMSO-d6) d ppm 1.29 (s, 12 H) 3.13 (s, 3 H) 3.55 (s, 2 H) 6.99 (d, J= 7.82 Hz, 1 H) 7.53 (s, 1 H) 7.61 (d, J= 7.95 Hz, 1 H).

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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;,
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3484-35-3, Adding a certain compound to certain chemical reactions, such as: 3484-35-3, name is 5-Methylindolin-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 3484-35-3.

General procedure: To a solution of hydrazide 4 (10 mmol, 0.36 g) in ethanol (20 mL), the appropriate isatin (10 mmol) was added followed by a catalytic amount of acetic acid (0.5 mL) then the mixture was refluxed for 1 h. The formed precipitate was filtered off, washed with hot ethanol and recrystallized from DMF/ EtOH to give the targeted compounds 5a-d. 4.1.3.4 4-(3-(2-(5-Methyl-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (5d) Yellow powder, 77% yield; mp > 300 C. IR (KBr) numax/cm-1 3344-3215 (NH2, NH), 1714, 1685 (C=O), 1517 (C=N), 1340, 1166 (SO2). 1H NMR (DMSO-d6, 300 MHz) delta 2.30 (s, 3H, CH3), 6.83 (d, 1H, J = 7.9 Hz, H-7 of isatin), 7.17 (d, 1H, J = 7.9 Hz, H-6 of isatin), 7.26 (s, 1H, H-4 of pyrazole), 7.27-7.35 (m, 5H, Ar-H), 7.49 (s, 2H, SO2NH2, D2O exchangeable), 7.57 (d, 2H, J = 8.1 Hz, Ar-H), 7.65 (d, 1H, J = 7.8 Hz, H-4 isatin), 7.91 (d, 2H, J = 8.7 Hz, Ar-H), 10.81, 11.22 (2s, 1H, NH isatin, D2O exchangeable), 11.54, 14.13 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz) delta 20.48 (CH3), 109.07, 110.87, 119.88, 121.29, 125.37, 125.90, 126.69, 128.54, 129.21, 131.68, 132.13, 138.08, 140.28, 141.34, 143.91, 145.43, 157.50, 162.61. MS m/z [%] 500 [M+, 5.60], 222 [100]. Anal. Calcd for C25H20N6O4S (500.53): C, 59.99; H, 4.03; N, 16.79; S, 6.41. Found: C, 60.23; H, 4.11; N, 16.93; S, 6.46.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
Indoline – Wikipedia,
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59-48-3, 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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (1.3 g) in 20 mL of acetonitrile was cooled to -10 C. and 2.0 g of N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of 5-bromo-2-oxindole. 1H NMR (360 MHz, DMSO-d6) delta10.44 (s, br, 1H, NH-1), 7.32-7.36 (m, 2H), 6.76 (d, J=8.5 Hz, 1H, H-7), 3.5 (s, 2H, CH2). MS m/z 212.1 and 214.1 [M and M+2]+.

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Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
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2913-97-5, Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5.

Example 28B; tert-butyl (2S, 3S)-2-{[2-(1, 3-dioXo-1, 3-dihydro-2H-isoindol-2-yl) ethyl] amino}-3- methylpentanoate; To a solution of Example 28A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2mL). The resulting solution was stirred for 3 hrs at 25¡ãC and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution washed with aqueous NaHC03 (2 x 300 mL). The organic layer was concentrated to give 12.9 g of the title compound.

According to the analysis of related databases, 2913-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/61487; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 1127-59-9

General procedure: Isatin 1 (3 mmol), malononitrile (3 mmol), 4-hydroxy-6-methylpyridin-2(1H)-one 2 (3 mmol) were refluxed for 60 minin ethanol (5 ml) with sodium acetate (10 molpercent) or in pyridine (without any catalyst). After the reaction was finished, the solid was filtered,washed with ice ethanol and dried to isolate pure products 3. For their characteristics, see Online Supplementary Materials.

The chemical industry reduces the impact on the environment during synthesis 1127-59-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Vereshchagin, Anatoly N.; Zaimovskaya, Tatiana A.; Korolev, Victor A.; Egorov, Mikhail P.; Mendeleev Communications; vol. 26; 5; (2016); p. 399 – 401;,
Indoline – Wikipedia,
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Some common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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. 1914-02-9

22d. 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline The product of 22c (200 mg, 1.35 mmol) and 2-fluoro-3-nitropyridine (0.3 mL) were pre-stirred in a conical microwave container. The mixture was heated at 200 C. under microwave with stirring at high absorption for 10 min. The cooled mixture was dissolved in EtOAc, washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, hexanes/EtOAc) to give pure 22d (220 mg, yield: 60.4%). LC-MS ESI 270 (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 1914-02-9, its application will become more common.

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
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