Tag: M.W=200-300

Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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. 15362-40-0

A finely ground mixture of chromone-3-carboxaldehyde(1 mmol) and oxindole/indolinone (1-(2,6-dichlorophenyl)-2-indolinone)/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1.2 mmol) was irradiated in microwave oven for 1 min and completion of the reaction was monitored with TLC. Reaction mixture was washed with diethyl ether to get pure compounds 5-10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15362-40-0, its application will become more common.

Reference:
Article; Shaveta; Singh, Amrinder; Kaur, Matinder; Sharma, Surbhi; Bhatti, Rajbir; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 185 – 192;,
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2058-72-2, A common compound: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A two-necked round-bottom flask with a magnetic stirring bar was flushed with nitrogen at r.t. MgBr2 (225 mg, 1.2 mmol), an N-substituted isatin 1 (1.0 mmol), ethyl propiolate (2; 1.3 equiv) and freshly distilled CH2Cl2 (5.0 mL) were added to the flask. The suspension mixture was stirred at r.t. for 5 h before turning into a pale yellow, homogeneous solution. The reaction was quenched by the dropwise addition of 10 % aqueous NaHCO3 (3 mL). The resulting two phases were separated, and the aqueous phase was extracted with EtOAc (30 mL). The combined organic layer was then washed with brine, dried over anhydrous MgSO4 and concentrated. The obtained crude product was purified by silica gel column chromatography (EtOAc/hexane, 20:80) to afford the corresponding ester 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, 5-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lingam, Kandapalam Arun Prasath; Amutha, Periyasamy; Yuvaraj, Paneerselvam; Selvakumar, Kodirajan; Synthesis; vol. 50; 3; (2018); p. 599 – 606;,
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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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 3416-57-7

To a refluxed mixture of 4.63 M sodium methoxide in methanol (55.0 mL, 254 mmol) and methanol (500 mL) was added solid N-acethonylphthalimide (25.00 g, 123.0 mmol, from TCI) in one portion. After addition, the reaction was heated at reflux for 2 hours, then cooled at 0 C and neutralized with 1 N HCl. The resulting suspension was stirred at 0 C for 30 minutes and then filtered under reduced pressure, washed with a small amount of water and air dried. The resulting solid was further dried under vacuum, over P2O5, to give the desired product (21.2 g, 85%). LCMS calculated for CnHi0NO3 (M+H)+: m/z = 204.1; Found: 204.0.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; LI, Yun-Long; COMBS, Andrew, P.; YUE, Eddy, W.; LI, Hui-Yin; WO2011/75630; (2011); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 99365-40-9 name is 6-Bromoindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 99365-40-9

(293-1) 3,3-Dimethyl-6-bromoindolin-2-one A solution (50 ml) of 6-bromoindolin-2-one (3.18 g) in THF was cooled to -78 C. and 1.5 M lithium diisopropylamide (20 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction mixture was brought to room temperature and stirred for 1 hr. Then the reaction solution was cooled to -78 C. again and 1.5 M lithium diisopropylamide (10 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction solution was brought to room temperature with stirring. Then a saturated aqueous solution of ammonium chloride was added thereto and the resultant mixture was extracted with ethyl acetate. The residue was washed with hexane to give the title compound (3.35 g) as a white amorphous solid (yield: 93.0%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.38(6H, s), 7.05(1H, d, J=8.0Hz), 7.096(1H, d, J=1.6Hz), 7.169(1H, d, J=1.6Hz), 8.41(1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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3416-57-7,Some common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, molecular formula is C11H9NO3, 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.

Step 1: (E&Z)-2-(4-(Dimethylamino)-2-oxobut-3-en-1-yl)isoindoline-1,3-dione A mixture of 2-(2-oxopropyl)isoindoline-1,3-dione (2.03 g, 10 mmol) and 1,1-dimethoxy-N,N-dimethyl-methanamine (1.3 ml, 10 mmol) was irradiated by microwave at 180 C. for 20 minutes. The resulting solid was recrystallized from ethanol to provide the title product as a mixture of cis- & trans-isomers 2.34 g (91% yield). ESMS(M+1)=259.10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Oxopropyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
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675109-26-9, The chemical industry reduces the impact on the environment during synthesis 675109-26-9, name is 6-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

Preparation 117: 6-bromo-2-(cyclopropylmethyl)-2,3-dihydro-1 H-isoindol-1 -one (1710) (1711) A stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (350 mg, 1.65 mmol) and cyclopropylmethyl bromide (0.198 muIota_, 1.98 mmol) in DMF (6 mL) was cooled in an ice bath under nitrogen. Then NaH (99 mg, 2.48 mmol) was added in portions. The reaction was stirred for 1 hour and then quenched with NH4CI (sat., aq.). The mixture was extracted with IPA:CHCI3 (1 :3, x3). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under vacuum to yield the title compound as a brown oil (~30 % pure) which was used crude. MS: [M+H]+ = 266/268.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

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 6326-79-0.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield).

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
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3335-98-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3335-98-6 name is 1-Phenyloxindole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

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; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
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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 181140-34-1 as follows. 181140-34-1

To a solution of 2-[(2f?)-2-oxiranylmethyl]-1 H-isoindole-1 ,3(2H)-dione (2.Og, 10.0 mmol) in isopropyl alcohol (40 ml_) were added 2-chloro-4-fluorobenzenesulfonamide (2.51 g, 12.0 mmol) and pyridine (0.16 g, 2.0 mmol). The reaction mixture was refluxed for overnight. Solvent was removed and residue was purified by flash column chromatography on silica gel (Biotage, 0.5%-2% MeOH/CH2CI2) to provide the title compound (2.64 g, 55.0%).

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/29210; (2006); A2;,
Indoline – Wikipedia,
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