Category: indolines-derivatives

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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11NO

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmnol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mnixture. The reaction was stirred for 50 min., and then poured into water. The mixture was basified with sodium carbonate and then extracted with ethyl acetate (*3), dried (MgSO4), filtered, and evaporated to the title compound (0.89 g, 92percent) 1H NMR (DMSO-d6) delta 1.21 (s, 6H), 6.76 (d, 1H, J=8.22 Hz), 7.29 (dd, 1H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1H, J=2.03 Hz), 10.4 (s, 1H).

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 19155-24-9.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
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Related Products of 17702-83-9, These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-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: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 °C reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL× 3), the organic layer was extracted four times (30mL × 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
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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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C8H9Cl2N

A mixture of 2-chloro-N-(1 H-indazol-5-yl)-5 ,7-dihydro furo[3 ,4-d]pyrimidin- 4-amine (1.0 g ), ZiniI.8 g, 7.8 mmcl) and 5-chloroisoindoline hydrochloride (0.58 g, 2.6 mmol) in NMP (20 mL) was heated at 150 °C lbr 1 h. The reaction mixture was cooled to room temperature, filtrated and purified by HPLC to give the title compound (110 mg, 9.12percent). ?HNMR(400 MHz, DMSO-d6)oe 12.95(1 H, s), 8.83(1 H, s), 8.26 (1 H, s), 8.08 (1 H, s), 7.62 (1 H, d, J=8.80 Hz), 7.49 (1 H, d, J8.80 Hz), 7.34 (1 H, d, J7.60 Hz), 4.86-4.71 (8 H, m). MS (ES+) rn/e 405 (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; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, name: 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
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Electric Literature of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Indole-2,3-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol) and 5 mol% of Cu doped CdS NPs in ethylene glycol (10 ml) was introduced in a 50 ml round-bottomed flask. The flask was placed in the microwave cavity and subjected to irradiation for appropriate time at 80 C using a maximum power of 300 W. When the reaction was complete, the reaction mixture was extracted with ethylacetate; the organic layer was removed under reduced pressure to afford the crude product. The pure products were obtained by crystallization from ethanol.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Parewa, Vijay; Maheshwari, Shuchi; Rathore, Kuldeep S.; Journal of Molecular Catalysis A: Chemical; vol. 394; (2014); p. 244 – 252;,
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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 2436-29-5 as follows. COA of Formula: C11H9NO3

Step 11. 2-(3-{[1-(3-Benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione; The product from Step 10 (20), 42 mg (0.13 mmol) was dissolved in anhydrous CH2Cl2 followed by the addition of phthalimide protected 3-aminopropionaldehyde 33 mg (0.16 mmol) and 37 mg (0.18 mmol) of sodium acetoxyborohydride and finally 10 mul (0.18 mmol) of acetic acid. The reaction was left stirring at room temperature for 2.5 h. The solvent was evaporated and the product redissolved in ethyl acetate and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated and dried under high vacuum resulting in 63 mg (0.13 mmol, 94%) of 2-(3-{[1-(3-benzyl-4-oxo-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (21) as a white solid.

According to the analysis of related databases, 2436-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiron Corporation; US2005/228002; (2005); A1;,
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Related Products 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.

General procedure: A mixture of isatin 1a (0.1 mmol), (E)-4-phenylbut-3-en-2-one (2a, 0.1 mmol), arginine (0.01 mmol) in MeOH (1.0 mL) was stirred for 48 h at 25 C. After completion of the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using petroleum ether/ethyl acetate = 1:1 as the eluent to give 3a.

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:
Article; Yan, Tingting; Wang, Xiaoyan; Sun, Hongbao; Liu, Jie; Xie, Yongmei; Molecules; vol. 18; 12; (2013); p. 14505 – 14518;,
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Reference of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-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.

Intermediate 2B:; [00193] Potassium nitrate (1.215 g, 12.02 mmol) was added portionwise to a solution of Intermediate 2A (1.6 g, 12.02 mmol) in sulfuric acid (24 mL) at 0 0C over 10 min. The reaction mixture was stirred for 3 h at ambient temperature. The reaction mixture was poured onto ice and the resulting precipitate was washed with water and dried in vacuo to yield Intermediate 2B (1.85 g, 10.38 mmol, 86 % yield) as a beige solid.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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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. category: indolines-derivatives

Step 2 5-Amino-1,3-dihydro-indol-2-one 5-Nitro-1,3-dihydro-indol-2-one 30b (3.56 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) to the solution at room temperature. The reaction mixture was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 5-amino-1,3-dihydro-indol-2-one 30c (2.04 g, yield 68.9%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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. Recommanded Product: N-(6-Bromohexyl)phthalimide

2-[6-(4-phenyl-1-piperidinyl)hexyl]-1H-isoindole-1,3(2H)-dione: To the 500 ml RB-flask was added 4-phenylpiperidine hydrochloride (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 oC for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform: 2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H) +; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borowsky, Beth; Blackburn, Thomas P.; Ogozalek, Kristine; US2003/82623; (2003); A1;,
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