Category: indolines-derivatives

Electric Literature of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The chemical industry reduces the impact on the environment during synthesis 7-Fluoroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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Electric Literature of 35197-64-9, 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In this work, previously reported N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide derivatives (25a-e) [44] were obtained by activating the carboxylic acid group of 24 (1 eqv) by using n-propanephosphonic acid anhydride (T3P, 50% in EtOAc, 1 eqv). The reaction was carried out under argon atmosphere for 2hat 0C in dry methylene chloride. Then, distilled triethylamine (1.2 eqv) and the appropriate N-benzylamine (1.1 eqv) were added to the reaction mixture [57]. The reaction was continued at room temperature for 12h. The products were purified by column chromatography over silica gel (DCM/acetone=9:1) to yield 25a-e as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; ?mudzki, Pawe?; Fija?kowski, ?ukasz; Furga?a, Anna; Gryz?o, Beata; Hoefner, Georg C.; Kulig, Katarzyna; Malawska, Barbara; Malawska, Katarzyna; Nowaczyk, Alicja; Podkowa, Adrian; Rapacz, Anna; Sa?at, Kinga; Wanner, Klaus T.; Zar?ba, Paula; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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: j0444] A flame-dried 50-mE round-bottomed flask, equipped with a Teflon stir bar, was charged with 2-substituted N-aryl pyrrolidine (1 mmol, 1 equiv.), and degassed CH2C12:H20 (1:1, 25-mE). Then, sodium periodate (641.7 mg, 3.0 mmol, 3.0 equiv.) was added to the phenol solutionand the reaction was stirred for 4 h. Then, the reaction mixture was quenched by the addition of NaHSO4 (10 mE, 10% by weight aqueous solution), and the phases were separated, and the aqueous phase was washed with CH2C12 (3×20 mE). The organic fraction was dried over Mg504, filtered and concentrated in vacuo to afford a crude residue, which was purified using flash column chromatography (silica gel with 15% EtOAc in hexanes as eluant) to afford a white powder in 95% isolated yield.

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

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; LUMB, JEAN-PHILIP; ESGUERRA, KENNETH V.N.; (118 pag.)US2017/66711; (2017); 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H4F3NO3

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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Synthetic Route of 129487-92-9,Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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.

Part H. To tert-butyl-5-amino-1-indolinecarboxylate (1.90 g, 8.2 mmol) was added 5-bromovaleryl chloride (1.4 mL, 9.0 mmol) and 18 mL of THF. After stirring for 5 min at rt under N2, potassium tert-butoxide (9 mL, 9 mmol; 1.0 M in THF) was added in one portion, and the resulting brown solution was stirred under N2 for 30 min. A second portion of potassium tert-butoxide (9 mL) was added, and the resulting brown suspension was stirred for 15 min. An additional 0.10 mL-portion of 5-bromovaleryl chloride and a 4.5 mL-portion of potassium tert-butoxide were added, and the mixture was stirred for 30 min. The reaction was then poured into H2O (80 mL). The aqueous layer was washed with EtOAc (3*50 mL), and the combined organic layers were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated and the resulting residue was purified by radial chromatography (50% EtOAc in hexanes) to afford tert-butyl 5-(2-oxo-1-piperidinyl)-1-indolinecarboxylate as a pink solid (1.30 g, 50%). LRMS (AP+): 317.2 (M+H)+. 1H NMR (CDCl3) delta7.40-7.80 (br m, 1H), 7.01 (s, 1H), 6.97 (d, 1H), 3.94 (t, 2H), 3.55 (br m, 2H), 3.09 (t, 2H), 2.49 (br m, 2H), 1.91 (br m, 4 H), 1.52 (s, 9H).

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
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Synthetic Route of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a cooled to -10 C. suspension of imidazole (16.3 g, 0.24 mol) and PPh3 (31.5 g, 0.12 mol) in dry CH2Cl2 (160 mL) I2 (30.5 g, 0.12 mol) was added in portions. After the addition the formed suspension was stirred for 30 min at room temperature followed by addition of P1 (15.3 g, 0.08 mol) in portions. The reaction mixture was stirred for 24 h, then aqueous Na2S2O3 was added. Organic layer was consequently washed with water, brine, and dried over Na2SO4. After evaporation yellow-green residue was obtained, which was chromatographed (CH2Cl2/hexanes 1:2) on silica gel. Recrystallization of the final product from hexanes/acetone yielded 20.9 g (87%) of white fibers.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Hydroxyethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Koltun, Dmitry; Zablocki, Jeff; Vasilevich, Natalya; Migulin, Vasily; US2009/253693; (2009); A1;,
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Synthetic Route of 446292-08-6, 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 446292-08-6 as follows.

63.5 g of the compound 6 (0.15 mol) prepared in Example 4-2 was added to the reaction flask, ethanol (1000 mL), 80% hydrazine hydrate (0.825 mmol) was added dropwise at room temperature, then heated to reflux 2h, the reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. 1000 mL of water was added and the mixture was extracted twice with dichloromethane (500 mL x 2). The dichloromethane phase was dried over anhydrous sodium sulfate and filtered through suction. The filtrate was evaporated to dryness to give a white solid which was dried in vacuo to give compound 7 (45.9 g); the yield was 95.4% and the purity was 99.7%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Stock Co. Ltd.; Hou, Junkai; Wang, Yuehui; Li, Hua; (12 pag.)CN105801572; (2016); A;,
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Synthetic Route of 875003-43-3,Some common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, molecular formula is C9H6FNO2, 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.

A mixture 7-fluoro-1-methylisatin (K1.3.54 g, 19.8 mmol) and 3-(tert- butyldiphenylsilyloxy)propan-1 -amine (6.90 g, 22.0 mmol) in EtOH (50 ml_) was heated at 60 C for 2 h then concentrated to provide 9.55 g (100%) of product K2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoro-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; VOIGT, Johannes, H.; WO2008/137139; (2008); A1;,
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Application of 3484-35-3, The chemical industry reduces the impact on the environment during synthesis 3484-35-3, name is 5-Methylindolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of oxindole (3a-f, 0.3mmol), 1-alkyl-1H benzo[d]imidazole-2-carbaldehydes (7a-e, 0.33mmol) in ethanol (2mL), was added catalytic amount of piperidine. The reaction mixture was stirred at reflux until complete consumption of the oxindole observed by TLC. After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-ones 8a-z orange/yellow solids in moderate to good yields. Compounds 8c, 8f, 8i, 8l and 8o did not precipitated out from ethanol, were purified by column chromatography with silica gel (60-120) by using ethyl acetate:hexane (2:8 to 3:7). 4.1.1.13 (E)-5-Methyl-3-((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-one (8m) Orange solid, Yield 79%; mp: 266-268 C; FT-IR: (cm-1): 3183, 3056, 2916, 1702, 1612, 1321, 815, 737; 1H NMR (500 MHz, DMSO-d6): delta 10.59 (brs, 1H, NH), 9.35 (s, 1H, Ar-H), 7.84 (d, J = 8.1 Hz, 1H, Ar-H), 7.69 (d, J = 8.1 Hz, 1H, Ar-H), 7.55 (s, 1H, C=CH), 7.41-7.31 (m, 2H, Ar-H), 7.15 (d, J = 7.8 Hz, 1H, Ar-H), 6.79 (d, J = 7.8 Hz, 1H, Ar-H), 4.02 (s, 3H, CH3), 2.35 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3+DMSO-d6): delta 168.9, 147.5, 142.6, 141.0, 135.4, 131.4, 130.9, 129.9, 128.4, 123.9, 122.7, 120.9, 119.5, 117.3, 110.4, 109.1, 30.0, 20.8; HRMS (ESI): m/z calcd for C18H16N3O 290.1293, found 290.1279 [M+H]+; Purity: 99.2%.

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

Reference:
Article; Sharma, Pankaj; Thummuri, Dinesh; Reddy, T. Srinivasa; Senwar, Kishna Ram; Naidu; Srinivasulu, Gannoju; Bharghava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 584 – 600;,
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Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4, Computed Properties of C9H7NO2

A solution of N-methylisatin (322 mg, 2.0 mmol), indole (234 mg, 2.0 mmol), and K2CO3 (138 mg, 1.0 mmol) in aqueous DMF (H2O/DMF, 2:1, 5.0 mL) was heated to 50 oC for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was obtained as a white solid, 440 mg (79%).1-4 To a stirred solution of 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (278 mg, 1.0 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 oC. The reaction mixture was stirred at room temperature for 2 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), 3-hydroxy-1-methyl-3-(1-methyl-1H-indol-3-yl)indolin-2-one was obtained as a white solid, 200 mg (68%).1,4 A solution of 3-hydroxy-1-methyl-3-(1-methyl-1H-indol-3-yl)indolin-2-one (146 mg, 0.5 mmol) and p-cresol (162 mg, 1.5 mmol) in CH2Cl2 (3.0 mL) was stirred at room temperature in the presence of montmorillonite K-10 (438 mg, 300%, w/w) for 2 h. The reaction mixture was filtered through a pad of Celite and washed thoroughly with CH2Cl2. After removal of solvent and column chromatographic purification process (n-hexane/EtOAc, 5:1) 1a was obtained as a white solid, 138 mg (72%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylisatin, and friends who are interested can also refer to it.

Reference:
Note; Seo, Da Young; Lee, Sangku; Min, Beom Kyu; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 8; (2018); p. 1011 – 1014;,
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