Indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5, SDS of cas: 2913-97-5

Example 12d (0.4 g, 0902 mmol) and 2-(l,3-dioxo onidQlm-2- i)acetaldehyde (0.683 g, 3 J61 mmol) were combined in tetral^drof ran (9 J02 mL) under nitrogen , cooled to 0 * C and treated drop-wise with 1M ntaniuin(I V) chloride in die hloro me thane (3 J61 mL, 3.61 mmol) to give an opaque red solution. The sotitionwas stirred for 72 hours at ambient temperature and partitioned b etween ethyl acetate and water. The organic layer was was hed with s aturated aqueous s odium chloride, dried over arLhydrous sodium sulfate, filtered and concentrated. -ificationby chromatography (siEca gel, 0.5-5percent methanol in dichloiomethane) afforded the title confound as a yellow powder (0.45 g, 81percent). NMR (500 MHz, DMS 0-^) 6 1 1.78 ^, ; = 1 S3 Hz, 1 7.93 (d, J = 1 .53 Hz, 1H), 7B1 – 7.85 (m, 4 7.76 (s, l H), 7.24 – 7.30 (m, 1 H), 721 (dd, J = 824, 1.83 Hz, 1H), 7.09 – 7.15 (m, 1H) 699 – 7.05 (m, 1 6.96 (d, J = 2.44 Hz, 1 HI 6.92 (d, J = 824 Hz, 1 HI 5.44 (dd, J = 9.92, 5 4 Hz, 1 HI 4.51 – 4.56 (m, 1H), 4.44 – 4.48 (m, 1 3.87 (dd, J = 13.28, 5.34 Hz, 1 HI 3 J66 (S, 3H), 3 2 (dd, J = 13.28, 10.22 Hz, 1H), 2.98 (s, 3H) . Xi (EpsilonXi 1+) m/z 615 (M+H) 1.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
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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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., COA of Formula: C8H4N2O4

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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; Muller, George; Man, Hon-Wah; Cohen, Benjamin M.; Li, Ying; Xu, Jean; Leong, William W.; US2012/232100; (2012); A1;,
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Synthetic Route of 7477-63-6, The chemical industry reduces the impact on the environment during synthesis 7477-63-6, name is 7-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.

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

Reference:
Article; Shang, Jian-Li; Guo, Hui; Li, Zai-Shun; Ren, Biao; Li, Zheng-Ming; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 724 – 727;,
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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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., name: N-Vinylphthalimide

b) Ethyl 2-[3-(2-amino-ethyl)-phenoxy]-2-methyl-propionate (13b); 10d (14 g, 49 mmol) is placed in the presence of N-vinylphthalimide (11 g, 63 mmol) and 27 ml (194 mmol) of triethylamine in 160 ml of DMF. Pd(OAc)2 (0.3 g) and P(oTol)3 (0.4 g) are added and the reaction medium is stirred for 10 h at 110 C. The reaction medium is dry concentrated and the residue obtained is taken up in water and extracted with AcOEt. After drying on MgSO4, the organic phases are dry concentrated and the oil isolated is purified by flash chromatography on silica (heptane:AcOEt 90:10). 11.5 g of oil is obtained (62% yield) then placed in a solution of 70 ml of THF and 70 ml of EtOH in the presence of Pd/C under hydrogen at 6 bar. This mixture is stirred for 72 h at ambient temperature. After filtration on celite, the reaction medium is dry concentrated and the residue obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 80:20). 10.9 g of clear oil are obtained (yield=94%). This oil is then placed in 140 ml of EtOH in the presence of 3.5 ml of hydrazine hydrate then this solution is heated at reflux for 4 h. After filtration of the insolubles, the reaction medium is dry concentrated and then the residue obtained is purified by flash chromatography on silica (CH2Cl2:MeOH:NH4OH 90:9:1). 5.7 g of intermediate 13b are thus isolated in the form of an oil (yield=80%). TLC silica gel 60 F 254 Merck, CH2Cl2:MeOH:NH4OH 90:9:1, Rf=0.28.

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; Pierre Fabre Medicament; US2008/167313; (2008); A1;,
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Related Products of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isatin 1 (147.1 mg, 1 mmol), (E)-1-phenylpent-2-ene-1,4-dione (2a, 348.4 mg, 2 mmol), and thiourea I (57 mg, 0.1 mmol) were cooled to -20 °C, dissolved in toluene (3 mL), and the mixture was stirred at -20 °C for 24 h. The progress of the reaction was monitored by TLC and NMR spectroscopy. The product was isolated by direct column chromatography on silica gel (CH2Cl2/EtOAc 95:5 to 85:15)

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Trubitson, Dmitri; ?ari, Sergei; Kaabel, Sandra; Kudrjashova, Marina; Kriis, Kadri; Jaerving, Ivar; Pehk, Tonis; Kanger, Tonis; Synthesis; vol. 50; 2; (2018); p. 314 – 322;,
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Adding a certain compound to certain chemical reactions, such as: 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, 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 35197-64-9, Safety of 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Step b: Preparation of tert-but 2-bromo-4-(l,3-dioxo-l,3-dihydro-2H-isoindol-2-yl) butanoate To a solution of compound obtained from Step a (180 mg, 0.576 mmoles) in tetrahydrofuran (5 mL) was added Boc anhydride (1 mL, 0.461 mmoles) and N,N- dimethylaminopyridine (7 mg, 0.057 mmoles). The reaction mixture was allowed to stir at room temperature for about 18 hours. After completion of reaction, solvent was azeotropically distilled using toluene and ethyl acetate to obtain a crude product. The crude product was purified on silica gel column using 20% ethyl acetate: hexane as eluent to get the desired product. Yield: 180 mg

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; PALLE, Venkata P.; SATTIGERI, Viswajanani; SATTIGERI, Jitendra; SONI, Ajay; RAUF, Abdul Rehman Abdul; SIVAKUMAR, R.; REDDY, Ranadheer R.; MUSIB, Arpita; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38944; (2012); A1;,
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6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. COA of Formula: C8H4BrNO2

5-bromo-2-ethylisoindoline-1,3-dioneTo a solution of 5-bromoisoindoline-1 ,3-dione (1 130 mg, 5 mmol) in THF (25 mL) was added iodoethane (0.606 mL, 7.50 mmol) and then slowly was added NaH (144 mg, 6.00 mmol). The resulting reaction was stirred at RT for 22 h. To the reaction mixture was added DMF (2 mL) then stirred at RT for 23 h. To the reaction mixture was added more DMF (3 mL) then was stirred at RT for 120 h. The reaction mixture was diluted with H20 (20 mL), acidified with HCI (1 mL, 1.0 N), extracted with EtOAc (3 x 20 mL), washed with brine (20 mL), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product 5-bromo-2-ethylisoindoline-1 ,3-dione (899.7 mg, 3.54 mmol, 70.8 % yield). LC-MS mlz 254.1 (M+H)+, 0.90 min (ret. time).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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Electric Literature of 18711-15-4, A common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, 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.

2.25 g of magnesium for a Grignard reaction in 15 ml of anhydrous THF are placed in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 13.6 g of 5-bromobenzofuran in 35 ml of anhydrous THF is then added. The mixture is stirred for one hour, followed by addition of a solution of 5 g of 4,6-dichloro-1H-indole-2,3-dione in 50 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out, dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.2 g of expected product are obtained. TLC: 6/4 hexane/EtOAc, Rf=0.35

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; SANOFI; US2012/40996; (2012); A1;,
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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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

To a stirred solution of 200 mg (0.87 mmol) of 2-(3-oxocyclopentyl)isoindoline-1,3-dione (CAS 1029691-06-2) in 5 mL of DCM at 0C were added 10mg (0.26 mmol) of NaBH4 and then lmL of MeOH. Themixture was stirred at this temperature for 0.5 h. 20 mL of H20 was added and the mixture was extractedwith DCM. The combined organic layers were dried over Na2SO4 and then concentrated under vacuum. The residue was purified by silica gel column chromatography (PE/ EA = 2/1) to give 96 mg of the product as a white solid.MS (ESI+): 232.0 [M+H].?H NMR (400 MHz, DMSO-d6) ppm: 7.76-7.83 (m, 5H), 4.80 (d, J = 5.2 Hz, 1H), 4.43 (m, 1H), 4.06 (m, 1H), 1.64-2.15 (m, 6H).

The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
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Application of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Reference Example 15 methyl 1-(6-chloropyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylate; A mixture of methyl 2,3-dihydro-1H-indole-5-carboxylate (5.19 g), 4,6-dichloropyrimidine (4.37 g), and ethanol (50 mL) was stirred overnight with heating under reflux, and concentrated under reduced pressure. To the residue were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the mixture was stirred for 30 min. Insoluble materials were collected by filtration to give the title compound (5.87 g, 69%) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:3.32 (t, J=8.7 Hz, 2 H), 3.91 (s, 3 H), 4.08 (t, J=8.7 Hz, 2 H), 6. 66 (s, 1 H), 7.90 (s, 1 H), 7.95 (d, J=8.5 Hz, 1 H), 8.46 (d, J=8.5 Hz, 1 H), 8.64 (s, 1 H).

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
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