Tag: M.W=100-200

Electric Literature of 60434-13-1, A common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

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:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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Related Products of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

356 mg of 5-nitro-1,3-dihydro-indol-2-one is hydrogenated in 30 ml of tetrahydrofuran_ethanol=1:1 with 400 mg palladium on carbon (10%) at room temperature and normal pressure for 1 hour. After catalyst is suctioned off on diatomaceous earth and after concentration by evaporation, 320 mg (100% of theory) of 5-amino-1,3-dihydro-indol-2-one is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindolin-2-one, its application will become more common.

Reference:
Patent; Schering AG; US2004/39019; (2004); A1;,
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Reference of 172078-33-0, 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 172078-33-0 as follows.

Compound 2-2: To a solution of 1-chloroisoquinoline-5-sulfonylchloride (0.4 g, 1.53 mmol) in DCM (10 mL) was added TEA (318 muL, 2.29 mmol) and indolin-5-ol (226.9 mg, 1.68 mmol). The mixture was stirred at 25 C. for 12 h under an N2 atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 1:1). Compound 2-2, 1-[(1-chloro-5-isoquinolyl) sulfonyl]indolin-5-ol (350 mg, 970.0 mumol, 63.6% yield), was obtained as a yellow solid.

According to the analysis of related databases, 172078-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cervello Therapeutics LLC; Lee, Matthew Randolph; Varano, JR., Anthony Joseph; (53 pag.)US2020/140412; (2020); 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. 366453-21-6, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 366453-21-6

k Synthesis of 2,3-dihydro-1H-isoindol-1-one (29): To a solution of 4-hydroxy 2,3-dihydro-1H-isoindol-1-one (27) (0.250 gm, 1.67 mmol) in DMF (5 ml) K2CO3 and was added, followed by addition of methyl bromoacetate, and the reaction mixture was stirred at room temperature for 2hr. Then the reaction mixture was then poured on ice and extracted with ethyl acetate (2*15 ml). After the standard workup, the residue was dissolved in methanol (3 ml), and treated with NaOH (5 ml, 1N) at 0 C. and then stirred for and additional hour. After the standard workup, the solid was recrystallized in methanol to give compound 29 (0.140 gm, 60%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 366453-21-6.

Reference:
Patent; Jagtap, Prakash; Southan, Garry; Salzman, Andrew; Szabo, Csaba; Ram, Siya; US2002/95044; (2002); A1;,
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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 317-20-4 as follows. SDS of cas: 317-20-4

General procedure: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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Electric Literature of 5428-09-1, 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 5428-09-1 as follows.

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

According to the analysis of related databases, 5428-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
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Synthetic Route of 41910-64-9, 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 41910-64-9 as follows.

General procedure: 5.1.25. 7-Fluoro-5-(methylsulfanyl)-2,3-dihydro-1H-indole (16f) To a stirred solution of potassium thiocyanate (14.0 g, 145 mmol) in MeOH (150 mL) was added bromine (3.80 mL, 72.3 mmol) dropwise at 0 C under N2 atmosphere. After the mixture was stirred for 15 min, a solution of compound 15f (9.00 g, 65.7 mmol) in MeOH (100 mL) was added and the resulting mixture was stirred at room temperature for 3 h. A solution of potassium hydroxide (18.4 g, 329 mmol) in water (120 mL) was added slowly to the mixture followed by stirring at 43 C for further 30 min. The reaction mixture was cooled to 10 C, and then iodomethane (4.10 mL, 65.7 mmol) was added. The resulting mixture was stirred at room temperature for 30 min. After the mixture was concentrated under reduced pressure, the residue was partitioned between CH2Cl2 and water. The organic layer was separated, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/CH2Cl2 = 2/1 to 1/1) to give the title compound (2.80 g, 23%). 1H NMR (400 MHz, CDCl3) delta 2.42 (3H, s), 3.05 (2H, t, J = 8.4 Hz), 3.62 (2H, t, J = 8.4 Hz), 6.85 (1H, d, J = 10.8 Hz), 6.93 (1H, s).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sato, Kenjiro; Sugimoto, Hiromichi; Rikimaru, Kentaro; Imoto, Hiroshi; Kamaura, Masahiro; Negoro, Nobuyuki; Tsujihata, Yoshiyuki; Miyashita, Hirohisa; Odani, Tomoyuki; Murata, Toshiki; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1649 – 1666;,
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Synthetic Route of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
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Application of 25369-33-9,Some common heterocyclic compound, 25369-33-9, name is 7-Chloroindolin-2-one, molecular formula is C8H6ClNO, 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: DMF-DMA (2.66 mL, 20.0 mmol) was added to a solution of the appropriate indole (0.78 mmol) in toluene (3 mL). The mixture was stirred for 2-4 h. The precipitate was collected by filtration and washed with dichloromethane.

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

Reference:
Article; Praveen Kumar; Gut, Jiri; Guedes, Rita C.; Rosenthal, Philip J.; Santos, Maria M.M.; Moreira, Rui; European Journal of Medicinal Chemistry; vol. 46; 3; (2011); p. 927 – 933;,
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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.

[0590] Procedure: To a stirred solution of 4-chloro-7-methoxyquinoline (0.05 g, 0.25 mmol) in 1,4- dioxane (5 mL) were added 5-nitroindoline (0.046 g, 0.28 mmol), cesium carbonate (0.25 g, 0.77mmol) and Xanthphos (0.029 g, 0.051 mmol). The resulting mixture was purged with argon for 15 min and added Pd2(dba)3 (0.023 g, 0.025 mmol) was added and the mixture was purged for another 10 min. Resulting mixture was stirred for 16h at 100 C. Progress of the reaction was monitored by TLC. Reaction mixture was filtered through celite bed and filtrate was diluted with ethyl acetate (20mL), washed with water (2 x 10mL) followed by brine (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified by combiflash using 55-60% ethyl acetate in hexane to afford 7-methoxy-4-(5-nitroindolin-1-yl)quinoline as yellow solid (0.12 g, 75%).1HNMR (400 MHz, DMSO-d6): delta 8.83 (d, J = 4.4 Hz, 1H), 8.08 (s, 1H), 7.91-(d, J = 8.8 Hz, 1H), 7.73 (d, J = 9.2 Hz, 1 H), 7.46 (s, 1H), 7.36 (d, J = 4.8 Hz, 1H), 7.23 (d, J = 9.2 Hz, 1H), 6.24 (d, J = 8.8 Hz, 1H), 4.26 (t, J = 8.4 Hz, 2H), 3.93 (s, 3H), 3.32 (t, J = 8.4 Hz, 2H); LCMS (ES) m/z = 322.1 [M+H]+.

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-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Indoline – Wikipedia,
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