Category: indolines-derivatives

Reference of 4702-13-0, These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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.

7-b: 1-Bromo-3-phthalimide acetone 2-Phthalimide acetic acid 2.05 g (10.0 mmol), 10 mL of thionyl chloride,Placed in 50mL reaction flask, reflux to the remaining raw materials, vacuum drying, in a brown oil, add 2mL toluene. 15 mL of 50% by weight aqueous solution of KOH was added to 40 mL of diethyl ether, and 6.00 g (33. Mmol) of nitrosourea was slowly added in portions under ice-cooling. After addition, shaking was continued for 10 minutes. , & Lt;And dried for 2 hours in the form of flake KOH to obtain a solution of diazomethane in diethyl ether.The above-mentioned diazomethane-containing ether solution was placed in a 100 mL reaction flask and placed in an ice bath. 2 mL of a toluene solution containing the above oil was slowly added dropwise. The reaction was complete, filtered, rinsed with diethyl ether and the resulting solid spare. The solid was dissolved in 20 mL of tetrahydrofuran, and 2 mL of a 40 wt% aqueous solution of HBr was added dropwise to the reaction mixture, and the mixture was dried under reduced pressure. Add 100mL ethyl acetate, placed in a separatory funnel, respectively, saturated NaHC03, water, saturated NaCl solution, dried anhydrous Mg2S04. Dried under reduced pressure and recrystallized from 95% by weight ethanol to give 1.24 g of a white solid in 44.0% by weight yield.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Union Pharmaceutical Factory; Institute of Materia Medica, Chinese Academy ofMedical Sciences; Pan, Xiandao; Zhang, Peicheng; Yang, Yajun; Zhao, Limin; (20 pag.)CN102786464; (2016); B;,
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Application of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
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Synthetic Route of 875003-43-3, These common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-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.

General procedure: First phenylacetylene (1 mmol) was stirred with Et3N (1 mmol) in CH3CN (5 mL) at roomtemperature. After 15-20 min, N-methyl isatin (1 mmol) and InBr3 (15 mol %)was added and the reaction mixture was stirred for 16-18 h. When N-methylisatin was completely consumed as indicated by TLC, phenyl-N-tosylmethanimine(1 mmol) was added and the reaction mixture was stirred untilthe reaction reached completion, as evidenced by TLC. Acetonitrile wasdistilled out under reduced pressure and the residue was purified by silicagel (mesh 60-120) chromatography (hexane-EtOAc) to afford thecorresponding products. Characterization data of representative compounds.

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Siddiqui; Rahila; Rai, Pragati; Waseem, Malik A.; Abumhdi, Afaf A.H.; Tetrahedron Letters; vol. 56; 29; (2015); p. 4367 – 4370;,
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Application of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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: 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.

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; 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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Related Products of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 25c (2.00 g, 6.94 mmol) and 7a (2.00 g, 10.6 mmol) in THF (70 mL) was added NH4OAc (5.40 g, 70.0 mmol) in MeOH (50 mL). The reaction mixture was stirred at room temperature for 3.5 h. A saturated aqueous solution of NaHCO3 was added to the reaction mixture and extracted with EtOAc three times. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 60-80percent EtOAc/n-Hexane, on silica gel eluting with 5percent MeOH/CHCl3, and on silica gel eluting with 65percent EtOAc/CHCl3 to afford 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione as a pale yellow powder (1.90 g, 60percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.8 Hz, 3 H), 5.08 (s, 2 H), 6.74 (br s, 1 H), 7.71 – 7.94 (m, 6 H), 8.16 (d, J = 8.5 Hz, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 458 [M+H]+, 30percent, 480 [M+Na]+, 100percent, 456 [M-H]-, 100percent. To a suspension of 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (1.88 g, 4.11 mmol) in EtOH (45 mL) was added hydrazine monohydrate (2.12 g, 42.3 mmol). The reaction mixture was stirred at room temperature for 1 day. MeOH, CHCl3, and NH-silica gel were added to the reaction mixture and concentrated. The residue was purified by column chromatography on NH-silica gel eluting with 5percent MeOH/CHCl3 and on silica gel eluting with 10percent MeOH/CHCl3 to 28percent aqueous ammonia/MeOH/CHCl3 (1/10/100) to afford 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine as a pale yellow amorphous (761 mg, 57percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 1.1 Hz, 3 H), 4.12 (s, 2 H), 6.72 (d, J = 1.1 Hz, 1 H), 7.87 (dd, J = 8.5, 1.7 Hz, 1 H), 8.17 (dd, J = 8.5, 0.5 Hz, 1 H), 8.45 (br s, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 328 [M+H]+, 100percent, 326 [M-H]-, 100percent. To a solution of 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine (600 mg, 1.83 mmol) and NEt3 (370 mg, 3.66 mmol) in CHCl3 (15 mL) was added dropwise n-butyryl chloride (0.21 mL, 2.02 mmol) at 0 oC. The reaction mixture was stirred at 0 oC for 0.5 h. Water was added to the reaction mixture and extracted with CHCl3 twice. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with EtOAc to 10percent MeOH/CHCl3. The amorphous obtained was crystallized from EtOAc/n-Hexane to afford 20 as a yellow powder (441 mg, 61percent): mp 190.0-191.0 oC; 1H NMR (300 MHz, DMSO-d6, delta): 0.89 (t, J = 7.4 Hz, 3 H), 1.47 – 1.63 (m, 2 H), 2.14 (t, J = 7.5 Hz, 2 H), 2.34 (d, J = 0.9 Hz, 3 H), 4.36 (d, J = 5.6 Hz, 2 H), 7.15 (d, J = 0.9 Hz, 1 H), 8.08 (br s, 1 H), 8.14 (d, J = 8.5 Hz, 1 H), 8.34 (br t, J = 5.6 Hz, 1 H), 8.85 (br s, 1 H), 9.43 (s, 1 H), 12.72 (br s, 1 H); MS (ESI) m/z 398 [M+H]+, 100percent, 420 [M+Na]+, 20percent, 396 [M-H]-, 100percent; Anal. Calcd for C19H19N5OS20.2H2O: C, 56.89; H, 4.88; N, 17.46. Found: C, 57.04; H, 4.88; N, 17.17.

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
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Adding a certain compound to certain chemical reactions, such as: 1127-59-9, name is 7-Methylindoline-2,3-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 1127-59-9, Quality Control of 7-Methylindoline-2,3-dione

General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in ‘solvent-free’ manner or with additive (‘on-solvent’ manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E.; Arkivoc; vol. 2018; 4; (2018);,
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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. Recommanded Product: 6-Chloroisatin

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, m.p. 196-198 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4556672; (1985); A;; ; Patent; Pfizer Inc.; US4569942; (1986); A;; ; Patent; Pfizer Inc.; US4690943; (1987); A;,
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These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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. COA of Formula: C10H11NO

EXAMPLE 10 5-Bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one: 3,3-Dimethyl-1,3-dihydro-2H-indol-2-one (1.12 g, 6.95 mmol) was dissolved in chloroform and stirred at room temperature under nitrogen. Bromine (1.12 g) was added and the mixture was heated under reflux until HBr evolution ceased and the bromine colour was discharged from the solution. The solution was washed with sodium metabisulphite solution and sodium hydrogen carbonate solution, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give 5-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a yellow solid. 1 H NMR (CDCl3) d1.39 (6H s), 6.8 (1H d), 7.3 (2H m), 7.9 (1H broad)

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company Limited; US5773448; (1998); A;,
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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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClNO4S

To a slurry of 2,3-dioxomdoline-5-sulfonyl chloride (Lee, D. et al. J. Med. Chem. 2001, 44, 2015) (7,07 g, 28.8 mmol) m CH2Cl2 (288 mL) at rt was added neopentyl alcohol (7.61 g, 86.3 mmol) then pyridine (11.6 mL, 143 mmol). The reaction was stirred at rt for 22 hours, becoming a clear, oiange solution. The reaction was diluted with ILO (300 mL) and extracted with EtOAc (2 chi 600 mL). The combined organic extracts were washed with 0.1 M aqueous HCl (3 * 300 mL), saturated aqueous NaHCO3 (300 mL), and saturated aqueous NaCl (300 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound as a yellow solid (6.40 g, 92%). 1H NMR (400 MHz, CDClj): consistent; MS (ES ) m’z 315.1 (,VHH2O)

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 132898-96-5.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); 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 41910-64-9 as follows. Recommanded Product: 41910-64-9

General procedure: To the appropriate cyclic amine (20 mmol) in hexane (15 mL) amyl nitrite (60 mmol, 7 g, 8 mL) was added in one portion. The resulting mixture was stirred for 30 min at room temperature. The precipitated solid was collected by filtration, washed with hexane, dried and used for preparation of corresponding N-aminoindolines 3a-d and N-amino-1,2,3,4-tertahydroquinolines 7a,b without purification.

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; S?czewski, Franciszek; Wasilewska, Aleksandra; Hudson, Alan L.; Ferdousi, Mehnaz; Rybczy?ska, Apolonia; Boblewski, Konrad; Lehmann, Artur; Acta poloniae pharmaceutica; vol. 72; 2; (2015); p. 277 – 287;,
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