Tag: M.W=200-300

20780-72-7, 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. 20780-72-7 name is 4-Bromoisatin, 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: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 ¡ãC (ice bath), whereupon sodium hydride (60percent dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 ¡ãC for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90percent-100percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
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5332-26-3, 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. 5332-26-3 name is 2-(Bromomethyl)isoindoline-1,3-dione, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Bromomethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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20780-72-7, Name is 4-Bromoisatin, 20780-72-7, 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.

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
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897957-06-1, name is 6-Bromo-1-methylindolin-2-one, 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. 897957-06-1

To I-3.2 (91 mg, 0.40 mmol) in anhydrous dioxane (8 mL) is added R5 (155 mg, 0.61 mmol) and potassium acetate (120 mg, 1.22 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (33 mg, 0.040 mmol) added and heated to 80 C. for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The residue is purified via column chromatography (cyclohexane/EA=1:1). Yield 100%. m/z 274 [M+H]+, rt 0.71 min, LC-MS Method b.

Statistics shows that 897957-06-1 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-1-methylindolin-2-one.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; US2013/172327; (2013); A1;,
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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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 99365-40-9

Pottasium tert-butoxide (0.085 g, 0.8 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (4.00 mL, 44.4 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.0 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85 C for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid. LRMS (m/z): 292/294 (M-1)-. 1H-NMR delta (DMSO-d6): 1.99-2.08 (m, 2H), 2.13-2.22 (m, 2H), 2.41-2.50 (m, 2H), 2.82-2.92 (m, 2H), 7.07 (d, J=3.0 Hz, 1 H), 7.21 (dd, J=9.0 and 3.0 Hz, 1 H), 7.50 (d, J=9.0 Hz, 1 H), 10.70 (brs, 1H).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., 3416-57-7

(Synthesis of Intermediate 3)102 g (0.5 mol) of the intermediate 1 and 147 g (0.5 mol) of the intermediate 2 thus obtained were mixed with 500 ml of ethanol, and the mixture was stirred while cooled to 5 C. to 10 C. 201 ml of SM-28 (28% sodium methoxide methanol solution) was added dropwise to the dispersion. The temperature of the reaction solution was kept to 10 C. or lower. After dropwise addition, the mixture was allowed to warm to room temperature and stirred additionally for 30 minutes, and then, after addition of 20 ml of water, stirred as heated under reflux additionally for 4 hours. After reaction, the reaction solution was cooled to room temperature, and 750 ml of water was added dropwise, allowing precipitation of the crystal. The crystal was filtered, washed with water and dried. The crystal was washed ad dispersed and stirred in 1,000 ml of n-hexane, filtered and dried, to give 143 g of an intermediate 3 (yield: 82.2%).

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; FUJIFILM CORPORATION; US2012/238752; (2012); A1;,
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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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 923590-95-8

Step 1: preparation of benzyl 4-bromoisoindoline-2-carboxylate (compound 3a) To a solution of 4-bromoisoindoline hydrochloride (235 mg, 1.0 mmol) in THF (4 mL) was added TEA (355 mg, 0.49 mL, 3.5 mmol). The mixture was then cooled with ice-water bath. CbzCl (256 mg, 0.22 mL, 1.5 mmol) was added dropwise. The reaction mixture was stirred at rt overnight, then diluted with water (20 mL), and extracted with EtOAc (30 mL) twice. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to afford compound 3a (255 mg) as a pink solid. MS: calc’d 332&334 (MH+), measured 332&334 (MH+).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; The designation of the inventor has not yet been filed; (99 pag.)EP3623369; (2020); A1;,
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883-44-3, 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. 883-44-3 name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, 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.

A 50 ml round bottom flask was charged with aq. NaHCO3(0.05 M, 10 ml), aq. K2CO3(0.5 M, 10 ml) and CHCl3(5 ml). Alcohol 5 (16.02 g, 78.1 mmol) was dissolved in CHCl3(50 ml) and transferred to the reaction mixture followed by tetra-nbutylammonium chloride (4.34 g, 15.6 mmol), N-chlorosuccinimide (20.9 g, 156.1 mmol) and TEMPO (2.44 g, 15.6 mmol) and the reaction mixture was stirred vigorously at rt for 4.5 h. The phases were separated and the organic phase was washed with sulfate buffer (100 ml), NaHCO3(100 ml), and brine (100 ml), dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (35% EtOAc in n-heptane, v/v) gave aldehyde 9 (6.54 g, 38%) as a white amorphous solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Hydroxypropyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Domeyer, Svenja; Bjerregaard, Mark; Johansson, Henrik; Pedersen, Daniel Sejer; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 644 – 647;,
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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 3416-57-7 as follows. 3416-57-7

[00653] To a mixture of 89 (4.00 g, 19.7 mmol, 1.0 eq), 4-methylbenzenesulfonic acid (1.02 g, 5.91 mmol, 0.3 eq) and ethane-1,2-diol (20 mL) in toluene (20 mL) was stirred at 110 C overnight under nitrogen. The mixture was concentrated and the residue was purified by SGC (petroleum ether / ethyl acetate, 5 / 1) to afford the desired product 90 (2.90 g, 11.7 mmol, 59.5%) as a white solid.[00654] LCMS: ESI-MS: m/z: 248.2 [M+H1 RT = 1.49 mm. (Method A)

According to the analysis of related databases, 3416-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALPHARMAGEN, LLC; PUTMAN, David, G.; DASSE, Olivier; HOGENKAMP, Derk; (154 pag.)WO2016/144792; (2016); A1;,
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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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 4702-13-0

To a solution of phthaloylglycin (0.300 g, 1.46 mmol) in CH2Cl2 was added oxalyl chloride (1.480 g, 11.66 mmol) and DMF (0.010 g, 0.137 mmol) at 0 C. The mixture was stirred at 0 C for 30 min., then warmed to room temperature and stirred for 3 h. The solvent was removed under reduced pressure. The solid residue was dissolved in CH2Cl2 and evaporated under reduced pressure (this procedure was repeated three times). The crude product was dried under vacuum to afford a yellow sold (0.310 g, 95%). This compound was used for next reaction without further purification.1H NMR (500 MHz, CDCl3). delta 7.91 (dd, J = 5.5, 3.2 Hz, 2H), 7.79 (dd, J = 5.5, 3.1 Hz, 2H), 4.82 (s, 2H).

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
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