Month: December 2020

Electric Literature of 70478-63-6,Some common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 32B tert-butyl (1S)-2-{[5-(1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)pyridin-3-yl]oxy}-1-(1H-indol-3-ylmethyl)ethylcarbamate A solution of Example 32A (0.2 g, 0.31 mmol) and 6-bromophthalimide (0.084 g, 0.4 mmol) in DMF (2 mL) was treated with Pd2 dba3 (0.04 g, 0.02 mmol), tri-o-tolylphosphine (0.02 g, 0.01 mmol), and triethylamine (0.06 mL, 0.4 mmol). The reaction was heated to 75¡ã C. for 6 hours in a sealed tube and concentrated. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide the desired product (0.116 g, 55percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Bis(diphenylphosphino)ferrocene-palladium(II) dichloride (50 mg, 0.06 mmol) is mixed with potassium acetate (600 mg, 6.14 mmol) and bis(pinacolato)diboron (572 mg, 2.25 mmol) in a 5 mL microwave tube. The tube is purged 3 times with vacuum and nitrogen before adding a nitrogen degassed solution of 4-bromo-2,3-dihydro-isoindol-l-one (434 mg, 2.05 mmol) in 1,4-dioxane. Nitrogen is bubbled for 5 minutes through the mixture, and then the tube is sealed and heated to 85C for 16 hours. The reaction mixture is cooled to room temperature and filtered through a celite pad. The filtrate is evaporated to yield the title compound, which is used as such for the next step

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2008/65199; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is Indolin-2-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 59-48-3, category: indolines-derivatives

To a stined solution of oxindole (20 g, 150 mmol) in 100 mL of Conc. H2S04 at -15 Cwas added fuming HNO3 (9.47 g, 150 mmol) drop wise. The reaction mixture was allowed tomaintain the temperature at -15 C for 0.5h. After completion of the reaction, the reaction mixture was poured into crushed ice. The yellow solid precipitate out which was isolated by filtration and dried under vacuum (13 g, 48%). ?H-NMR (300 MHz, DMSO-d6) oe ii (s, 1H), 8.20-8.10 (m, 2H), 7.00 (d, J=8.4 Hz, 1H), 3.6 (s, 2H).LC-MS: mlz 177 (M-H).

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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UJJINAMATADA, Ravi Kotrabasaiah; SAMAJDAR, Susanta; HOSAHALLI, Subramanya; ABBINENI, Chandrasekhar; (70 pag.)WO2018/109650; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 350797-56-7, 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. 350797-56-7, name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 360 mg of compound A was dissolved in 50 ml MeOH and was reduced using 10% Pd/C catalyst in a commercial H-Cube reactor. Solution was passed through catalyst cartridge at 40C at a rate of 1 ml/min. Pressure = 1 bar.Reaction was complete in 60 minutes. Solution was concentrated to give 37 mg (67% yield) of product. HNMR was satisfactory.

The synthetic route of 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RATIOPHARM GMBH; GIDWANI, Ramesh Matioram; KOLHATKAR, Mayur Vilas; WO2011/124704; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 337536-15-9, A common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 solution of 4-bromoisoindolin-1-one (1.0 g, 4.72 mmol) and benzophenone hydrazone (2.78 g, 14.15 mmol) in 1,4-dioxane (25 mL) at room temperature under nitrogen, BINAP (587 mg, 0.94 mmol), palladium (II) acetate (212 mg, 0.94 mmol) and sodium t-butoxide (1.36 g, 11.15 mmol) were added and the mixture was heated at 100 C. for 16 h. The resultant mixture was cooled to room temperature, filtered, and the filtrate concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient). Pure fractions were combined and concentrated. The product was dried under reduced pressure to afford 4-(2-(diphenylmethylene)hydrazinyl)isoindolin-1-one, cpd 133a (1.544 g, 90.7% yield). MS m/z 328.0 (M+H)+

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-Bromoisoindolin-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 675109-26-9, Recommanded Product: 675109-26-9

A mixture of 6-bromoisoindolin-1-one (287 mg, 1.35 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (500 mg, 1.35 mmol), Pd(dppf)Cl2 (33 mg, 0.041 mmol) and Cs2CO3 (1.32 g, 4.05 mmol) in dioxane (50 mL) and water (8 mL) was heated to 100 C. overnight. After cooling, the mixture was concentrated under vacuum and purified by column chromatography on silica gel ((1%-3% MeOH in DCM) to afford 9A (220 mg, 76% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) delta 8.66 (s, 1H), 7.76-7.15 (m, 4H), 7.15 (s, 1H), 4.43 (s, 2H), 3.72 (s, 3H); ESI m/z 214.1 [M+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; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1074-82-4, 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows.

(a) The reaction mixture of p-bromobenzyl bromide (corresponding to 50) (4.00g, 16.004mmol) and phthalimide potassium salt (3.26g, 17.61mmol) in DMF (10ml) was stirred for 6h at 100C with a CaCl2 tube. After cooling, H2O (100ml) was added, and the resulting mixture was extracted with AcOEt (100ml¡Á3). The combined organic layer was washed with H2O (100ml¡Á1) and then brine (100ml¡Á1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford 2-(4-bromobenzyl)isoindole-1,3-dione (5.28g, quant. y.) as a colorless solid. Colorless cotton-like crystal (n-hexane/AcOEt). Mp 126-129C. 1H NMR (300MHz/CDCl3) delta 4.80 (2H, s, CH2), 7.32 (2H, d, J=7.8Hz, ArH), 7.44 (2H, d, J=8.1Hz, ArH), 7.71-7.73 (2H, m, ArH), 7.84-7.85 (2H, m, ArH).

The chemical industry reduces the impact on the environment during synthesis Potassium 1,3-dioxoisoindolin-2-ide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3720 – 3731;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl indoline-5-carboxylate

A glass microwave reaction vessel was charged with methyl indoline-5-carboxylate (0.06 g, 0.339 mmol), 2-cliloro-4-methyipyrimidine (0.054 g, 0.423 mmol),racemic-2,2′-bis(diphenyTphosphino)- I,’-tainaphthyl (0.032 g, 0.051 mmol), palladium (ii) acetate (7.60 mg, 0.034 mmol) and cesium carbonate (0.221 g, 0.677 mmol) in tetrahydrofuran (1.7 ml). The reaction mixture w’as purged with N2 and heated in a microwave reactor at 110 C for 10 min. LCMS showed desired product. The reaction mixture was diluted with water and extracted with DCM. The organic extract was washed with saturated NaCl and dried over MgSCb. The solution was filtered and concentrated in vacuo to yield cmde product which was used for next step directly m/z: 270.2 [M+l]

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; AMGEN INC.; CARMOT THERAPEUTICS, INC.; BUTLER, John R.; ERLANSON, Daniel; GRACEFFA, Russell; IWIG, Jeffrey; JEONG, Joon Won; WHITE, Ryan D.; WU, Yongwei; YI, Shuyan; BANERJEE, Abhisek; MCFARLAND, Jesse M.; ZHENG, Xiao Mei; (307 pag.)WO2020/36940; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)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. category: indolines-derivatives

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.61 2-((2-(2-(Octan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (9C) Brown powder, mp 65-70 C, 81% yield; 1H NMR (400 MHz, CDCl3): delta 0.89-0.91 (m, 4H, CH2, 3H, CH3), 1.53-1.62 (m, 3H, CH2), 1.93 (s, 3H, CH3), 2.24-2.35 (m, 2H, CH2), 2.44-2.47 (m, 1H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.72 (s, 2H, ArCH2), 7.70-76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 141452-01-9, name is Methyl indoline-5-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H11NO2

A mixture of compound 24a (500 mg, 2.82 mmol), 1-bromo-4-fluoro-benzene 24b (0.31 mL, 2.82 mmol), Pd2(dba)3 (129 mg, 0.14 mmol), BINAP (132 mg, 0.21 mmol), and sodium t-butoxide (325 mg, 3.39 mmol) in toluene (25 mL) was placed in a capped vial and heated at 80 C. overnight. The reaction mixture was then diluted with EtOAc and water, and the water layer was basified to pH8 with 1N aqueous NaOH. The organic layer was concentrated under reduced pressure and purified by flash column chromatography (silica gel, 5-30% EtOAc/heptane) to give a mixture of compound 24c (145 mg), MS m/z (M+H+) 272.1, and compound 24d (232 mg), MS m/z (M+H+) 258.0.

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

Reference:
Patent; Zhang, Yue-Mei; Connolly, Peter J.; Lin, Shu-Chen; MacIelag, Mark J.; US2012/101081; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem