Category: indolines-derivatives

Application of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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: A mixture of phthalimide10(6.8 mmol) dissolved in EtOH (20 mL) was gently boiled for about 1h. The hot solution was decanted from any solid into 1.25 mL of a specially prepared solution of KOH (15.25 g KOH dissolved in 15 mL of H2O and 45 mL of EtOH). A precipitate of potassium phthalimide separates at once. The mixture was stirred and cooled quickly to room temperature, and the precipitate was filtered under vacuum. To the alcoholic mother liquors a second 1 g portion of phthalimide was added, and the entire process was repeated. The two crops of crystals were united and washed with acetone to remove any unchanged phthalimide. After air-dried pure potassium phthalimidewas obtained as white crystals (yield 30%). In a second step, a mixture of potassium phthalimide (2.2 mmol),the appropriate dibromoalkane derivative (2.9 mmol) and 2.5 mL of acetone was stirred and refluxed for 24h, and then cooled to 15 C. After filtering off the precipitated potassium bromide, the cake was washed with acetone and the solvent evaporated to give pure compound.

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

Reference:
Article; Capela, Rita; Magalhaes, Joana; Miranda, Daniela; Machado, Marta; Sanches-Vaz, Margarida; Albuquerque, Ines S.; Sharma, Moni; Gut, Jiri; Rosenthal, Philip J.; Frade, Raquel; Perry, Maria J.; Moreira, Rui; Prudencio, Miguel; Lopes, Francisca; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 69 – 78;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

142.5 g (0.360 mol) of 2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino} propyl)-1 H-isoindole-1 , 3(2H)-dione (I), 175.32 g (1 .082 mol) of N,N- carbonyldiimidazole and 1425 mL of tetrahydrofuran were charged in a 3L flask and the reaction mass was heated to reflux for 4 hours. Then, the reaction mass was cooled down to 0 C for 1 hour and the resulting solid was filtered off and dried under vacuum at 70 C.Yield: 137.8 g. Molar yield: 90.73%. HPLC purity: 99.74%. M.P.: 223 C. S.O.R.: [a ]D25 = -75.26 (c = 1 ,DMSO)

The synthetic route of 446292-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS LESVI, S. L.; VISHNU NEWADKAR, Ravindranath; CHANGDEO GAIKWAD, Avinash; MADHUKAR HARAD, Ajay; DALMASES BARJOAN, Pere; WO2013/53739; (2013); A1;,
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Application of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 solution of 6-chloroindoline-2,3-dione (1 g, 5.51 mmol, SCRC) in anhydrousN,Ndimethylformamide (40 mL) was cooled to 00 C, whereupon NaH (60 % dispersion inmineral oil, 0.258 g, 6.44 mmol) was added in one portion and the reaction was stirred for 5 minutes. lodomethane (0.403 mL, 6.44 mmol) was added and the reaction mixture was stirred at 0 C for 30 minutes. The mixture was then poured into saturated aqueous NH4C1 and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give the crude product (1.2 g), which wasused without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloroisatin, its application will become more common.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; HARDEE, David; BREWER, Jason; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; SCHRIMPF, Michael; SHEPPARD, George; (139 pag.)WO2018/188047; (2018); A1;,
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Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

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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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. 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-(Hydroxymethyl)isoindoline-1,3-dione

6.1 5-Phthalimidomethyl-2,3,3-trimethylindolenine To a stirred solution of 2,3,3,-trimethylindolenine (20g, 126mmol) in concentrated sulphuric acid (100ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20g, 114mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84g, 87%).

According to the analysis of related databases, 118-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CARNEGIE MELLON UNIVERSITY; EP1042407; (2001); B1;,
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Application of 264916-06-5, 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 264916-06-5 as follows.

2-Boc-5-Aminoisoidoline (50 mg, 0.21 mmol) was added to a solution of NaOMe in MeOH (4 mL of0.26 M, 1.05 nimol) . This solution was then combined with a solution of paraformaldehyde (9.5 mg, 0.32 rnmol) in MeOH (2 mL) . The solution was stirred overnight (about 18 hours) at room temperature, after which time NaBH4 (8 mg, 0.21 mmol) was added and the reaction mixture was heated at reflux for 5 hours. After cooling to room temperature, the reaction was quenched with the addition of saturated aq. NH4C1 (1 mL), then diluted with water (about 20 mL) and extracted with CH2C12. The organic extracts were dried over Na2SO4. After removal of the solvent, the product was purified by flash chromatography (Si02, 15-45% EtOAc/hexanes gradient). Yield: 25.6mg (52%), pale yellow oil, Mixture of rotamers. ?H NMR (400 MHz, CDC13) 5 7.04 and 6.09 (d, J = 8.3 Hz, 1H) , 6.73 – 6.45 (m, 2H) , 4.72 – 4.47 (m, 4H) , 3.52 (s, 1H) , 1.50 (s, 9H) . ?3C NMR (151 MHz, CDC13) 5 148.0, 138.5, 123,6, 123.3, 113.6, 113.5, 107,1, 107.0, 79.7, 52.6,52.3, 52.0, 51.6, 31.9, 31.8, 28.71, 28.67. FIRESITOE m/z 249.1597 (014H20N202 + H, required 249.1597)

According to the analysis of related databases, 264916-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-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 104618-31-7, HPLC of Formula: C14H15NO3

A solution of 4-phthalimido cyclohexanol (7.1 g, 0.029 mole) in dichloromethane (250 ml) was treated with pyridinium chlorochromate (8.6 g, 0.04 mole) and the resulting dark mixture was stirred at room temperature overnight. Diethyl ether (50 ml) was added and the mixture filtered through keiselguhr. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2; CHCl3/EtOAc) to give 4-phthalimido cyclohexanone as a white solid (6.4 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
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These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-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. Recommanded Product: 5,7-Dimethylindoline-2,3-dione

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Part A. To the product (1.0 g, 4.2 mmol) from Example 2, Part B, was added N,N-dimethylglycine (490 mg, 4.7 mmol), triethylamine (1.80 ml, 13 mmol), and DMF (30 mL). To this mixture was added benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (2.2 g, 4.3 mmol). After 10 min, the clear yellow solution was poured into EtOAc (80 mL) and washed with H2O (2×50 mL). The organic layer was washed with brine, dried over Na2SO4, and filtered. The resulting residue was purified by radial chromatography (5% MeOH in CH2Cl2) to afford tert-butyl 5-[(N,N-dimethylglycyl) amino]-1-indolinecarboxylate (1.50 g, 110%) containing a small amount of DMF. LC/MS (ESI+): 320.1 (M+H)+.

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; Pinto, Donald J.P.; Han, Wei; Hu, Zilun; Qiao, Jennifer; US2003/232804; (2003); A1;,
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19155-24-9, name is 3,3-Dimethylindolin-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. Application In Synthesis of 3,3-Dimethylindolin-2-one

Under an argon atmosphere, to a solution of 3,3-dimethylindolin-2-one (0.050 g, 0.31 mmol) in N,N-dimethylformamide (1.0 ml) was added sodium hydride (0.012 g, 60 wt percent oil dispersion) under ice-cooling. After stirring for 30 min, 2-(5-bromomethyl-2-chlorophenyl)-4-methoxy-6-phenyl-1,3,5-triazine (0.10 g, 0.26 mmol) obtained in the above-mentioned (1) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture were added saturated aqueous ammonium chloride solution and ethyl acetate and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, washed with saturated brine, dried over sodium sulfate, filtered to remove sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=7/2) to give the title compound (0.11 g, yield 89percent). (0610) 1H-NMR (400 MHz, CDCl3) delta: 1.44 (6H, s), 4.18 (3H, s), 4.98 (2H, s), 6.72-6.76 (1H, m), 7.02-7.08 (1H, m), 7.13-7.19 (1H, m), 7.21-7.25 (1H, m), 7.31-7.36 (1H, m), 7.46-7.53 (3H, m), 7.55-7.61 (1H, m), 8.00 (1H, br s), 8.51-8.58 (2H, m).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; Nagamori, Hironobu; Mitani, Ikuo; Yamashita, Masaki; Hotta, Takahiro; Nakagawa, Yuichi; Ueda, Masatoshi; US2015/266834; (2015); A1;,
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