Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-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 2058-72-2, Recommanded Product: 5-Bromo-1-methylindoline-2,3-dione

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 50-60 min. After cooling, the solid products 20were filtered off and crystallized from iPrOH.

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; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

13220-46-7, name is 4-Methylindolin-2-one, 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. SDS of cas: 13220-46-7

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 4-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 80 mg (52%) of the title compound as a brown solid.1HNMR (360 MHz, DMSO-d6): delta 13.33 (s, br, 1H, NH-1′), 10.84 (s, br, 1H, NH-1), 7.54 (s, 1H, H-vinyl), 7.12 (d, J=2.0 Hz, 1H, H-2′), 7.01 (t, J=7.75 Hz, 1H, H-6), 6.79 (d, J=7.75 Hz, H-5), 6.74 (d, J=7.75 Hz, 1H , H-7), 2.64 (t, J=7.65 Hz, 2H, CH2CH2COOH), 2.57 (s, 3H, CH3), 2.42 (t, J=7.65 Hz, 2H, CH2CH2COOH), 2.19 (s, 3H, CH3); MS m/z (relative intensity, %) 311 ([M+1]+, 100).

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 56341-37-8, 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. 56341-37-8 name is 6-Chlorooxindole, 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.

[Step 1] (3E/Z)-6-chloro-3-[(2-chloro-3-fluoropyridin-4-yl)methylene]-1,3-dihydro-2H-indol-2-one [0083] N,N-Diisopropylethylamine (0.46 ml, 2.63 mmol) was added to a methanol (130 ml) solution of 6-chloro-1,3-dihydro-2H-indol-2-one (2.20 g, 13.11 mmol) and 2-chloro-3-fluoroisonicotinaldehyde (2.20 g, 13.8 mmol) and the resulting mixture was heated to reflux for 16 hours. After cooling, the precipitate was collected by filtration, washed with cold methanol and dried to give 3.37 g (83%) of the title compound as a solid. MS (APCI) m/z: 309 (M+H)+.

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

Reference:
Patent; Daiichi Sankyo Company, Limited; YOSHIDA, Shoko; SUGIMOTO, Yuuichi; EP2894156; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9NO

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized from methanol or acetone to give compound (1-19).

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2, These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-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.

Example 7 4-Chloro-N-amino phthalimide STR34 To a cooled mixture of 1.81 g (10 mmol) 4-chloro phthalimide in 20 mL ethanol (96%) was added 0.5 mL (10 mmol) hydrazine monohydrate. The reaction mixture was stirred for 2 min. at room temperature and 2 min. at reflux. By adding 50 mL cold water pale yellow crystals formed alter 1 h. Resulting crystals was filtered and recrystallized from ethanol to give 0.4 g (20%) 4-chloro-N-amino-phthalimide:

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hay; Allan S.; Ghassemi; Hossein; US5359092; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, 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. Safety of 6-Nitroindoline

1-Methyl-2,3-dihydro-1H-indol-6-ylamine. 6-Nitroindoline (2 mmol) was combined with methyl iodide (2.2 mmol), n-Bu4I (7.4 mg, 0.020 mmol), and K2CO3 (350 mg, 2.5 mmol) in acetone (10 mL). The mixture was stirred at 25 C. for 16 h. The mixture was partitioned between CH2Cl2 and satd. aq. NaHCO3 (20 mL), and the organic layer was dried and concentrated. Purification by silica gel chromatography provided 1-methyl-6-nitroindoline (300 mg, 84%).

The synthetic route of 6-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carruthers, Nicholas I.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A.; US2005/70534; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 110568-64-4, name is 6-Nitroisoindolin-1-one, 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 110568-64-4, Formula: C8H6N2O3

Step C / Intermediate B8: 5-aminoisoindoiin-1 -oneTo a solution of 5-nitroisoindolin-1 -one (60 mg, 0.337 mmoi) in methanol (20 mL) was added palladium on carbon (10 %, 50 mg). The mixture was stirred under an atmosphere of hydrogen for 1 hour. Filtration through Celite, followed by concentration led to 5-aminoisoindoiin-1 -one as a tan solid (38 mg, yield 78.2 %).

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; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; CHENG, Liang; LIU, Xijie; HU, Yuandong; XU, Xinhe; LIU, Zhihua; ZHANG, Lipeng; WU, Wei; WANG, Shulong; SHEN, Yu; LI, Gen; WANG, Yin; ZHAO, Sheng; LI, Chonglong; TANG, Jia; YU, Honghao; WO2012/92880; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, COA of Formula: C8H8N2O2

REFERENCE EXAMPLE 3 Preparation of N-(2,3-dihydro-1H-indole-5-yl)-methansulfonamide 5-nitroindoline (100 mg, 0.61 mmol) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml). Ammonium formate (192 mg, 3.05 mmol, 5 equivalent) and palladium/carbon (10%) in a catalytic amount were added at room temperature and refluxed at 40 C. for ten minutes. After completing the reaction, the reacting solution was filtrated through celite and concentrated under reduced pressure. Afterward, water (5 ml) was added to the residue, extracted consecutively 4 times with ethyl acetate (10 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then dried completely under a high-degree vacuum. The obtained compound, namely (2,3-dihydro-1H-indole-5-yl)-amine, was dissolved in dichloromethane (5 ml). Then, trimethylamine (0.063 ml, 0.45 mmol) was added to be cooled to -20 C. and mesyl chloride (0.035 ml, 0.45 mmol) was added to be stirred for 30 minutes at the same temperature. Water (5 ml) was added to separate dichloromethane solution, dried over anhydrous magnesium sulfate, purified through a flash column chromatography (an eluent: ethyl acetate/n-hexane=2/1, v/v) and then triturated with isooctane. As a result, the present compound (60 mg, productive yield 47%) was obtained as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta2.00 (s, 3H), 3.15 (t, J=8 Hz, 2H), 3.95 (t, J=8 Hz, 2H), 7.25 (d, J=8 Hz, 1H), 7.45-7.60 (m, 4H), 7.80 (s, 1H), 7.95 (d, J=8 Hz, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Patent; CHEIL JEDANG Corporation; US2003/109568; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 603-62-3, 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. 603-62-3 name is 3-Nitrophthalimide, 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.

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 x 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Nitrophthalimide, and friends who are interested can also refer to it.

Reference:
Patent; Celgene Corporation; MULLER, George, W.; SCHAFER, Peter, H.; MAN, Hon-Wah; ZHANG, Ling-Hua; GANDHI, Anita; CHOPRA, Rajesh; EP2683384; (2015); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, 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.

To a mixture of 3,3-dimethyloxindole 41 (150 mg,0.93 mmol, 1.00 equiv) and Cs2CO3 (606 mg, 1.86 mmol, 2.00 equiv) in THF (4.70mL) was added o-nitrobenzyl bromide (302 mg, 1.40 mmol, 1.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 6 mL) and washed with brine. The combined organic phases were driedover MgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?2-nitrobenzyl-3,3-dimethyloxindole 3a (258 mg, 93percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 (dd, J = 8.1, 1.4Hz, 1H), 7.51 (td, J = 7.6, 1.4 Hz, 1H), 7.44 (dddt, J = 8.1, 7.4, 1.4, 0.7 Hz, 1H), 7.28(ddd, J = 7.3, 1.3, 0.6 Hz, 1H), 7.17 (td, J = 7.7, 1.3 Hz, 1H), 7.12 (dq, J = 7.8, 1.0Hz, 1H), 7.09 (td, J = 7.5, 1.1 Hz, 1H), 6.61 (dt, J = 7.8, 0.8 Hz, 1H), 5.33 (d, J = 0.8Hz, 2H), 1.48 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.8, 148.2, 141.4, 135.8,134.2, 132.0, 128.5, 128.0, 127.6, 125.7, 123.2, 122.8, 108.8, 77.2, 44.5, 41.2, 24.8;IR (Neat Film NaCl) 2968, 1721, 1615, 1524, 1489, 1385, 1338, 1177, 1008, 858, 761cm-1; HRMS (MM: ESI-APCI+) m/z calc?d for C17H17N2O3 [M+H]+ : 297.1234;found: 297.1236.1 Vu, A. T.; Cohn, S. T.; Zhang, P.; Kim, C. Y. Mahaney, P. E.; Bray, J. A.; Johnston, G. H.; Koury, E.J.; Cosmi, S. A.; Deecher, D. C.; Smith, V. A.; Harrison, J. E.; Leventhal, L.; Whiteside, G. T.;Kennedy, J. D.; Trybulski, E. J. J. Med. Chem. 2010, 53, 2051?2062.NHOo-nitrobenzyl bromideCs2CO3THF, 23 °C(93percent yield)NOO2N4 3a

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem