Author: Jessica.F

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. category: indolines-derivatives

Step 1: synthesis of methyl 4-(4-methylindolin-2-on)ylsalicylate (1-2) (0094) (0095) 4-Methylindol-2-one (147 mg, 1 mmol) and methyl 4-iodosalicylate (306 mg, 1.1 mmol) were dissolved in 2 mL dioxane, followed by adding cuprous iodide (38 mg, 0.2 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium carbonate (415 mg, 3 mmol). The mixture was heated by microwave at 125C to react for 120 min. The mixture was cooled to room temperature, diluted with 20 mL ethyl acetate, filtered, and evaporated under reduced pressure to remove the solvent. The residue was separated by column chromatography (silica gel 200-300 mesh, eluent: n-hexane/ethyl acetate = 4/1) to give 70 mg methyl 4-(4-methylindolin-2-on)-ylsalicylate as a yellow solid with a yield of 23.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13220-46-7, its application will become more common.

Reference:
Patent; Beijing Hanmi Pharmaceutical Co., Ltd.; XUE, Hai; ZHAO, Tao; CHA, Mi Young; KIM, Maengsup; (40 pag.)EP3252038; (2017); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO3

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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Reference of 496-12-8, A common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

Conc. H2SO4 (8 mL) was added dropwise at 0 C to a solution ofisoindoline (19) (2 g) in DCM (10 mL), and the reaction mixturewasstirred at rt for 10 min. DCM was evaporated under vacuum fromthe reaction mixture and conc. HNO3 (2 mL) was added dropwise at0 C. The reaction mixture was stirred for 2 h at rt. Ice water wasadded to the reaction mixture then the reaction mixture wasbasified with sodium bicarbonate. Extraction was done with EtOAc(100 mL x 3) and the combined organic layer was dried overanhydrous MgSO4 and concentrated under reduced pressure to give 20 in 50% yield; 1H NMR (300 MHz, CDCl3): d 8.07e8.12 (m, 2 H),7.34 (d, J 8.5 Hz, 1H), 4.32 (s, 4H).

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ojha, Ritu; Nepali, Kunal; Chen, Chun-Han; Chuang, Kuo-Hsiang; Wu, Tung-Yun; Lin, Tony Eight; Hsu, Kai-Cheng; Chao, Min-Wu; Lai, Mei-Jung; Lin, Mei-Hsiang; Huang, Han-Li; Chang, Chao-Di; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 190; (2020);,
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Electric Literature of 3891-07-4, 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 3891-07-4 as follows.

General procedure: To the stirred solution of hydroxyderivatives (0.1 mol) in anhydrous DMF (50 mL) sodiumhydride (60% in mineral oil) (4.4 g, 0.11 mol) was added with mechanistic stirring between -5 and0 C. After addition, stirring was continued for 2 h at room temperature. Carbon disulfide (9 mL,0.15 mol) was added dropwise at 0 C. The reaction mixture was warmed to room temperature andstirred for 5 h. The color of the one was gradually changed to dark red. The reaction mixture wascooled to 0 C and methyl iodide (7.8 mL, 0.12 mol) was added dropwise. The mixture was warmed toroom temperature, stirred for 3 h until the color changed from dark red to yellow and poured into ice(100 g), extracted with CH2Cl2 (3 50 mL). The extract was washed with water (3 50 mL) and driedwith MgSO4. After removal of the solvent the product was washed with hexane and dried in vacuum.3.2.1. O-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] S-Methyl Dithiocarbonate 1dYield 27.8 g (99%). Yellow powder: mp 105-106 C. 1H-NMR (400 MHz, CDCl3): delta 2.49 (s, 3H, SCH3),4.10 (t, 3J = 5.6 Hz, 2H, CH2), 4.82 (t, 3J = 5.6 Hz, 2H, CH2), 7.71-7.73 (m, 2H, arom H), 7.83-7.86 (m, 2H,arom H). 13C-NMR (125 MHz, DMSO-d6): delta 18.4 (s, SCH3), 36.3 (s, CH2), 70.6 (s, CH2), 123.2 (s, arom.C), 131.6 (s, arom. C), 134.6 (s, arom. C), 167.7 (s, C=O), 215.2 (s, C=S). LC-MS, m/z: 282 [M + H]+.Anal. calcd for C12H11NO3S2: C, 51.23; H, 3.94; N, 4.98; S, 22.79; found: C, 51.30; H, 4.00; N, 4.98; S,22.70.

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sokolenko, Taras M.; Dronkina, Maya I.; Magnier, Emmanuel; Yagupolskii, Lev M.; Yagupolskii, Yurii L.; Molecules; vol. 22; 5; (2017);,
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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. 20780-72-7, name is 4-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H4BrNO2

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
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Related Products of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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 5,6-dimethoxy-2-[(E)-1-arylmethylidene]-1-indanone (1, 0.364 mmol), thiazolidine-4-carboxylic (3, 0.364 mmol) and 1-morpholinoindoline-2,3-dione (2,0.364 mmol) was dissolved in methanol (1 mL) and irradiated for 2-3.5 min in a CEM microwave synthesizer (100 0C, 100 W). After completion of the reaction as evident from TLC, the mixture was poured into water. The precipitated solid was filtered and washed with water to afford the products 4a-i which was purified by recrystallisation.

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

Reference:
Article; Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Sellappan, Velmurugan; Elumalai, Karthi Keyan; Pandian, Suresh; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7418 – 7421;,
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Synthetic Route of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To the mixture of 6-chloro-2-oxindole (11 g, 65.6 mmol) (Crescent) and 3-chloro-2-fluorobenzaldehyde (12 g, 75.7 mmol) (Aldrich) in methanol (140 mL) was added piperidine (5.59 g, 65.6 mmol) (Aldrich) dropwise. The mixture was then heated at 50 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-2-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 18 g, 89%).

The synthetic route of 6-Chlorooxindole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
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Application of 65435-04-3, A common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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.

EXAMPLE 13 (FROM TABLE 3) 3-[4-(2-Carboxy-ethyl)-3-methyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxindole (6.7 g) was added to a stirred suspension of 23 g aluminum chloride in 30 mL dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed to 40..50 C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

The synthetic route of 65435-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Some common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, molecular formula is C8H3F2NO2, 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. Product Details of 774-47-0

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 774-47-0, its application will become more common.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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Electric Literature of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred mixture of isatins 3a-c (3.4 mmol), potassium carbonate(0.94 g, 6.8 mmol) and catalytic amount of potassium iodidein dry DMF (10 mL), the appropriate alkyl halide 5a-d (3.7 mmol) or benzyl bromide 5e (0.63 g, 3.7 mmol) was added, and the mixture was heated under reflux for 3 h. Then, the reaction mixture was poured into ice-water, the obtained solid was collected, washed several times with water, and recrystallized from ethyl alcohol to afford the N-substituted isatin derivatives 6a-o [27].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Bonardi, Alessandro; Bua, Silvia; Ibrahim, Hany S.; Elaasser, Mahmoud M.; Kry?tof, Vladimir; Jorda, Radek; Gratteri, Paola; Abou-Seri, Sahar M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 184; (2019);,
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