Month: November 2020

Adding some certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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 2436-29-5. 2436-29-5

To a solution of 2 (300 mg, 1.04 mmol) and 11a (317 mg, 1.56 mmol) in THF (30 mL) was added NH4OAc (802 mg, 10.4 mmol) in MeOH (30 mL). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-3% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow solid (437 mg, 89%): MS (ESI) m/z 472 [M+H]+, 100%, 470 [M-H]-, 100%.

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 3-(1,3-Dioxoisoindolin-2-yl)propanal.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Koami, Takeshi; Takayama, Tetsuo; Yabuuchi, Tetsuya; Katakai, Hironori; Ikeda, Akiko; Aoki, Mari; Naruse, Takumi; Wada, Reiko; Nozoe, Akiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7128 – 7138;,
Indoline – Wikipedia,
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1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. 1074-82-4

2-(6-bromohexyl)isoindoline-1,3-dione (10). To a stirred solution of 1,6-dibromohexane (9) (16.5 g, 67.5 mmol) in acetone (100 mL) was added potassium phthalimide (5.00 g, 27.0 mmol). The resulting mixture was refluxed for 24 hours. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. MPLC purification of the residue (Hexanes:EtOAc/70:30) gave 10 as a colorless oily liquid (6.3 g, 75%). 1H NMR (400 MHz, CDCl3) delta 7.85-7.83 (m, 2H), 7.72-7.70 (m, 2H), 3.68 (t, J=7.2 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 1.89-1.82 (m, 2H), 1.73-1.66 (m, 2H), 1.52-1.45 (m, 2H), and 1.41-1.33 (m, 2H).

Statistics shows that 1074-82-4 is playing an increasingly important role. we look forward to future research findings about Potassium 1,3-dioxoisoindolin-2-ide.

Reference:
Patent; Pang, Yuan-Ping; Park, Jewn Giew; Wang, Shaohua; Vummenthala, Anuradha; Mishra, Rajesh K.; Davis, Jon; Millard, Charles B.; Schmidt, James J.; US2012/114696; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5,Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

A mixture of intermediate B2 (i .46 g, i equiv), hydroxylamine hydrochloride (0.64 g, i .2 equiv), anhydrous K2C03 (i.6 g, i.5 equiv) in absolute methanol (iO ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water, extracted with dichloromethane three times. The organic phase was combined and washed with brine, dried and solvent evaporated to give the title compound as a white solid (0.75 g). ?H-NMR (d5-DMSO, 400 MHz, ca i:i cis-trans isomer) 64.30/4.37 (2xd, 2H, J=4.0), 6.8i/7.35 (2xt, iH, J=4.0), 7.8i-7.88 (m, 4H), iO.86/ii.34 (2xs, iH); MS (El) mlz: 204 (Mj.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(2-Oxoethyl)phthalimide, its application will become more common.

Reference:
Patent; Shen, Jianhua; Wang, Yiping; Wang, Kai; US2014/171431; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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.

Under an inert gas atmosphere, add a stir bar, 0.75 mmol of 1-methylisatin, 0.05 mmol of DBU, and 2 mL of acetonitrile to the autoclave, and then fill the autoclave with carbonyl sulfide gas of about 0.8MPa. After stirring for 24 hours at , the autoclave was opened, the reaction solution in the autoclave was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round-bottomed single-neck flask, with (3¡Á2 ml) dichloromethane The autoclave was rinsed, and then the solvent was removed in vacuo to obtain a crude product.The crude product was separated and purified by column chromatography (eluent: dichloromethane).The yield was 91%.

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 2058-74-4.

Reference:
Patent; Dalian University of Technology; Zhou Hui; Chen Wei; Lv Xiaobing; (10 pag.)CN111233741; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8.

To a solution of 6-bromo-4-chlorobenzo[c][l ,2,5]oxadiazole (372 mg, 1.6 mmol) in NMP (3 mL) in a 4 dram vial was added isoindoline (238 mg, 2 mmol) and triethylamine (400 muL¡¤, 2.9 mmol). A cap was tightly fitted and the reaction was heated at 85 C O/N. The reaction was worked up by diluting with EtOAc (60 mL) and washing with 1M HCl (3 x 20 mL) and brine (1 x 20 mL). The organic phase was dried with MgS04 filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (9 : 1 Hex / EtOAc) to give 208 mg (41 % yield) of 6-bromo-4-(isoindolin-2-yl)benzo[c][l ,2,5]oxadiazole. lU NMR (300 MHz, CDC13) delta = 7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H). To a solution of the afore mentioned material, (200 mg, 0.6 mmol) in DME (4 mL) / Na2C03 (0.9 mL) was added 3- formyl-phenylboronic acid (134 mg, 0.9 mmol) and Pd(P(Ph)3)4 (35 mg). The flask was then fitted with a reflux condenser, purged with argon and heated to 115 C O/N. The reaction was worked up by diluting with 1 M NaOH (40 mL) and extracting with EtOAc (3 x 20 mL). The organic phase was washed with brine, dried with MgS04 and concentrated in vacuo. The crude material was fused to Si02 (2 g) and purified by flash column chromatography (2:1 DCM / Hex) to give 190 mg (92 % yield). 1H NMR (500 MHz, CDC13) delta = 10.18 (s, 1H), 8.24 (m, 1H), 7.99 (dm, J = 8 Hz, 2H), 7.70 (t, J = 7 Hz, 1H), 7.44 (m, 4H), 7.26 (s, 1H), 6.30 (s, 1H), 5.25 (s, 4 H). To a stirring solution of the afore mentioned material, (190 mg, 0.55 mmol) and Rupert’s reagent (150 mg, 1.1 mmol) in DCM (5 mL) at 0 C was added TBAF (0.1 mL, 1 M THF, 0.1 mmol). After 30 min at low temperature the cold bath was removed and the reaction was allowed to come to RT. After 3 hours an excess of TBAF was added and the reaction was diluted with DCM. The organic phases were washed with saturated NFLCl, brine, and then dried with MgS04 and concentrated in vacuo. The crude material was passed through a plug of Si02 (DCM)and then purified by flash column chromatography (2: 1 DCM / Hex). 1H NMR (500 MHz, CDCI3) delta = 7.84 (s, 1H), 7.77 (dt, J = 7 Hz, 2 Hz, 1H), 7.60 (m, 2H), 7.43 (m, 4H), 7.23 (s, 1H), 6.25 (s, 1H), 5.31 (s, 4H), 5.2 (m, 1H), 2.68 (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 496-12-8.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; WOOD, Thomas, K.; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2014/31873; (2014); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

General procedure: A mixture of isatin (1.0 mmol), alpha-amino acid (1.0 mmol) and aroylacrylic acid (1.0 mmol) in 4.0 mL aqueous methanol(1:3) was heated in an oil bath to reflux temperature for about 20 min or stirred at room temperature from 25 min to 12 hours. The resulting precipitates were collected by filtration and washed with cold methanol to give analytically pure products 6.

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 5-Bromo-1-methylindoline-2,3-dione.

Reference:
Article; Pavlovskaya, Tatyana L.; Yaremenko, Fedor G.; Lipson, Victoria V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Musatov, Vladimir I.; Karpenko, Alexander S.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 117 – 126;,
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. 2058-74-4, name is 1-Methylisatin, This compound has unique chemical properties. The synthetic route is as follows., 2058-74-4

General procedure: To a mixture of indole-2,3-dione 1a (1.0 mmol) and o-aminothiophenol 2 (1.0 mmol) in distilled water (5.0 mL), was added TBAB (0.0483 g, 15 mol %). This reaction mixture was allowed to stir magnetically at 60 C. Progress of the reaction was monitored by TLC (Pet. ether-ethyl acetate = 4:1) and visualization was accomplished in an iodine chamber. After completion of the reaction, the solid obtained was collected by filtration and washed with warm water. The crude product, so obtained was purified by crystallization with ethanol to afford pure product.

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:
Article; Jain, Renuka; Sharma, Kanti; Kumar, Deepak; Tetrahedron Letters; vol. 53; 46; (2012); p. 6236 – 6240,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

104618-32-8, 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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 11 3-Amino-6-(N-methylsulphonamidomethyl)-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (0.42 g) with 4-(N-methylsulphonamidomethyl) phenyl hydrazine hydrochloride (0.44 g), and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.15 g), mp 218-222 C. dec.

The synthetic route of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2436-29-5 name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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. 2436-29-5

Step 5. 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 15 (31 mg, 1 eq.) in CH2Cl2 (3 ml), was added aldehyde 16 (0.8 eq., 17 mg), sodium triacetoxy borohydride, and acetic acid. The reaction mixture was stirred for 3 h at room temperature. Water was added and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to yield 46 mg of 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(1,3-Dioxoisoindolin-2-yl)propanal, and friends who are interested can also refer to it.

Reference:
Patent; Wang, Weibo; Constantine, Ryan N.; Lagniton, Liana Marie; Bair, Kenneth; US2005/261337; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

222036-66-0, 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. 222036-66-0, name is 5-Aminoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem