Tag: M.W=100-200

Reference of 32372-82-0, These common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, 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.

l-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (2 eq.) was added to a stirred solution of 30 (1 eq.), isoindoline hydrochloride (1.5 eq.), 1- hydroxybenzotriazole (2 eq.) N,N-diisopropylethylamine (2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 31 (82%) as a white amorphous solid. 1H- NMR (500 MHz, CDC13) delta 8.06 (s, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 5.32 (s, 1H), 5.01 (t, 1H), 4.46 (s, 4H), 3.87 (s, 3H), 3.11 (m, 2H), 2.06 (m, 2H).13C-NMR (125 MHz, CDC13) delta 169.5, 156.6, 143.9, 140.0 (2), 132.8, 129.1, 126.2 (2), 126.2 (2), 115.3, 61.9, 56.1 (2), 35.2, 19.7.

Statistics shows that Isoindoline hydrochloride is playing an increasingly important role. we look forward to future research findings about 32372-82-0.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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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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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);,
Indoline – Wikipedia,
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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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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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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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL×2) to afford the pure products as solid powder in good to excellent yields without further purification.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
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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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 39603-24-2

General procedure: A mixture of isatin (1 mmol), thiosemicarbazide/4-methyl-3-thiosemicarbazide (1 mmol) was taken in 5 cm3 watercontaining 20 mol% of [2-HMPyBSA]HSO4 and stirred atroom temperature for the time specified in Table 2. Theprogress of reaction was monitored by TLC. After completionof the reaction, the reaction mixture was filteredand washed with ethanol to yield corresponding product inpure form. Products were characterized by usual spectraltechniques. (i.e. IR, 1H, 13C NMR, and MS).

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; Korade, Suyog N.; Patil, Jayavant D.; Pore, Dattaprasad M.; Monatshefte fur Chemie; vol. 147; 12; (2016); p. 2143 – 2149;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., Formula: C10H13N

A mixture of 3,3-dimethylindoline (5s, 103 mg, 0.700 mmol), potassium carbonate (288 mg,2.084 mmol), and 2-bromopropanenitrile (303 muL, 3.506 mmol) in 2 mL CH3CN was stirred at 80C overnight. The mixture was concentrated and purified by preparative HPLC. Fractions containing productwere partly concentrated and residue was extracted with 1 M NaHCO3 and CH2Cl2. Organic phases weredried over MgSO4, filtered, and concentrated to give 2-(3,3-dimethylindolin-1-yl)propanenitrile (105mg). LCMS m/z = 201.2 [M+1]+; 1H NMR (400 MHz, CDCl3) delta ppm 1.26 (s, 3H), 1.40 (s, 3H), 1.63 (d, J = 7.3Hz, 3H), 3.05 (d, 1H, J = 8.2 Hz), 3.25 (d, 1H, J = 8.2 Hz), 4.57 (q, 1 H, J = 7.3 Hz), 6.57 (d, 1H, J = 7.9 Hz),6.83-6.87 (m, 1H), 7.06 (dd, 1H, J1 =7.4 Hz, J2 = 0.8 Hz), 7.12-7.16 (m, 1H).

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; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
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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. 61-70-1, name is 1-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Methylindolin-2-one

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

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 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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