Author: Jessica.F

These common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, 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 7-Bromooxindole

To a mixture of 7-bromoindolin-2-one (10 g, 48 mmol) and sodium carbonate (10 g, 96 mmol) in 1,4-dioxane (100 mL) was added 4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (7.3 g, 48 mmol) and Pd(PPh4)3 (2.5 g, 2.4 mmol) at room temperature. The mixture was heated to reflux and stirred under nitrogen overnight. On completion, the mixture was diluted with water (100 mL) and extracted with dichloromethane (3 x 200 mL). The combined organic layers were washed with brine (2 chi 200 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 6: 1 ] to give compound B-263 (6.8 g, 90% yield) as a yellow solid.

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

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 24566-79-8,Some common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(6-Bromohexyl)phthalimide, its application will become more common.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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. 1498-88-0, name is 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline] belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C19H18N2O3

General procedure: All spectroscopic analyses were performed with an Ocean OpticsUSB 4000 spectrometer and an LS-1 tungsten halogen lamp with a400 nm longpass filter. UV and visible light exposures were performedusing a UV-UVP lamp (4 Watt, 365 nm) and a Fisher ScientificUltra-bright LED Illuminator (18 mW, 400e750 nm)respectively. All spectroscopic analyses were carried out withconstant magnetic stirring at room temperature. Monomer solution spectra were measured using a quartz cuvette containing a 1 mLaliquot of a 1 103 M monomer solution in acetone. Polymerspectra were obtained by suspending a 5 mg quantity of polymer in2 mL of acetone in a 1 cm quartz cuvette. Absorbance spectra of theMC forms of dyes were recorded after exposure to UV light for1 min. The metal complex spectra were obtained by adding a 20 mLaliquot of a 0.02 M CoCl2 or ZnCl2 solution in acetone to the cuvetteafter 1 min of UV light exposure, and then recording the spectrum.Experiments to measure the rates of photochemical isomerizationfrom the SP to MC form (forward reaction) were conducted underconstant UV light, with absorbance measurements recorded at thewavelength of maximum absorbance (lmax) every 10 s for a total of10 min. To determine the rate of isomerization from the MC to SPform (reverse reaction), the cuvette was first exposed to UV light(solution 45 s; polymer 8 min) to convert the dye to the MCform. The reverse reaction was then monitored during constantvisible light exposure, with absorbance measurements recorded atlmax every 10 s for total of 15 min.

The synthetic route of 1498-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sennett, Kelly A.; Lindner, Brian K.; Kaur, Navdeep; Fetner, Shannon M.; Stitzel, Shannon E.; Dyes and Pigments; vol. 98; 3; (2013); p. 437 – 441;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Isoindoline 228 Milligram (mg) ( (1.91 mmol, mmol) was dissolved in dimethylformamide Dissolved in 20 milliliters (mL) 153 mg of 55% (v / v) sodium hydride at 0 C (3.52 mmol) was added thereto, followed by stirring for about 40 minutes, 3 – ((2S, 3R, 4R, 5S, 6R) -3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran -2-yl] benzyl bromide 800 mg (1.60 mils Mol) was added and the mixture was stirred at room temperature for about 10 hours. 100 milliliters of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate Dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography to give 420 mg (yield: 70.7%) of the title compound was obtained.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samjin Pharmaceutical Co., Ltd.; Cho, Eui-Hwan; Shin, Hui-Jong; Kwon, Ho-Seok; Lee, Jae-Woong; Joo, Jeong-Ho; Lee, Keun-Kuk; Kim, Jong-Min; Kim, Hyun-Tae; Kim, Jae-Eon; Lee, Jung-Rok; Jang, Beom-Hyeon; (37 pag.)KR2016/97861; (2016); A;,
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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H6BrNO2

General procedure: A mixture of isatin 1 (1 mmol) and malononitrile (2) (1 mmol) in EtOH (3 mL) was stirred for 15 min then treated with a solution of dialkyl acetylenedicarboxylate 3 (1 mmol) and 3,4-dimethylaniline (1 mmol) in EtOH (1 mL). The mixture was stirred at room temperature for 8 h. After completion of the reaction (TLC, eluent: EtOAc/hexane, 1:2), the mixture was filtered and the precipitate washed with H2O (5 mL) and EtOH (5 mL) to afford the pure product 4.

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 2058-72-2.

Reference:
Article; Tisseh, Zeinab Noroozi; Ahmadi, Fereshteh; Dabiri, Minoo; Khavasi, Hamid Reza; Bazgir, Ayoob; Tetrahedron Letters; vol. 53; 28; (2012); p. 3603 – 3606;,
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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

Step 2; 126 1272-(2-(benzyloxy)ethyl)isoindoHne-l,3-dione (127): A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70 % dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10 % – 20 % ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65 %).(ES, m/z) [M+H]+ 282.0; NMR (300 MHz, CDC13) 6 7.85 – 7.88 (m, 2H), 7.71 – 7.74 (m, 2H), 7.25 – 7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, J= 6.0 Hz, 2H), 3.74 (t, J= 6.0 Hz, 2H).

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest, J.; MU, Changwei; SELNICK, Harold, G.; SHI, Feng; VOCADLO, David, J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/64680; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7147-90-2, 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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added benzylmagnesium chloride (2 M in THF, 30 mL) dropwise at 0 C. After the addition, the reaction mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regio isomers (5.47 g, 100%). MS: 274.1 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 52351-75-4, These common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-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.

A mixture of 6-methoxyisatin(0.18g, 0.001 mol) in Anhyd. ethanol (2m1) and thiosemicarbazide(0.1g, 0.0011 mol) in a mixture of water (2 ml)andglacialacetic acid (0.5 ml) was irradiated under microwave irradiation at560W for 5-minutes. A yellowcoloured solid formed during irradiation. The solid was filtered, washed well with water andcrystallized from ethanol-DMF furnishing yellow crystals.yield 0.247g (95%), m.p. 265C.[Found : N, 22.68, S,12.62. C1DH,0N402S requires N, 22.40; S, 12.80%];IR: 825, 860 (1, 2, 4-trisubstituted benzene ring), 1115 (C=S), 1125 & 1370 (C-O-Cstretching), 1620 (C=N), 1700 (C=O), 3200, 3280, 3400 (NH, NH2).

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Ravinder; Oriental Journal of Chemistry; vol. 30; 1; (2014); p. 319 – 323;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 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.

Example 28 7-(((Benzo[1,3]dioxole-5-carbonyl)-amino)-methyl)-2-(oxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid; Phthalimidoacetaldehyde diethyl acetal (100 g, 0.38 mol) and 1 N hydrochloric acid (600 ml) was mixture was stirred at reflux temperature for 5 min. or until a homogeneous solution is obtained. The reaction mixture was cooled and the precipitate was filtered off and dried in vacuo at 50¡ã C. for 16 h which afforded 63.3 g (88percent) of phthalimidoacetaldehyde as a solid.1H NMR (300 MHz, CDCl3) delta 4.58 (s, 2H), 7.76-7.78 (m, 2H), 7.90-7.92 (m, 2H), 9.67 (s, 1H).To a mixture of phthalimidoacetaldehyde (64 g, 0.34 mol) and trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (81.5 g, 0.38 mol) in benzene (600 ml) stirred for 15 min. under nitrogen was added dropwise a 45percent solution of zinc chloride diethyl ether complex in dichloromethane (55.5 ml, 0.17 mol) at 0¡ã C. The reaction was allowed warm up to room temperature overnight. To the reaction mixture was added water (500 ml) and the resulting mixture was extracted with ethyl acetate (200 ml). The organic extract was washed successively with 1.0 N hydrochloric acid (2.x.200 ml) and brine (200 ml). The organic phase was dried (Na2SO4), filtered and the solvent evaporated in vacuo which afforded a slowly crystallising oil (98 g). To the solid was added a mixture of ethyl acetate and diethyl ether (400 ml, 1:1) and the resulting precipitate was filtered off, washed with a small portion of diethyl ether and dried at 50¡ã C. for 1 h affording 59.8 g (69percent of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid. The filtrate was evaporated in vacuo and the residue purified by column chromatography on silica gel (1 L) using a mixture of ethyl acetate and heptane (1:2) as eluant. Pure fractions were collected and the solvent evaporated in vacuo to almost dryness, the solid was filtered off and dried in vacuo at 50¡ã C. for 16 h affording an additional 15 g (17percent) of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.1H NMR (300 MHz, CDCl3) delta 2.61 (d, 2H), 3.85 (dd, 1H), 4.18 (dd, 1H), 4.76 (m, 1H), 5.43 (d, 1H), 7.28 (d, 1H), 7.69-7.77 (m, 2H), 7.84-7.88 (m, 2H).2-(4-Oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione (13 g, 0.051 mol) was dissolved in ethyl acetate (250 ml) and placed in a Parr bottle. 10percent Pd/C (1.5 g) was carefully added and the mixture was shaken under a pressure of 30 psi of hydrogen for 6.5 h (Parr apparatus). Filtration followed by evaporation of the ethyl acetate in vacuo afforded a crude 11.5 g of 2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione pure enough for the next step. Analytical pure compound could be obtained by purification of a small sample (250 mg) by column chromatography on silica gel, utilising a mixture of hexane/ethyl acetate as a gradient (from 100/0 to 50/50). Pure fractions were collected and the solvent evaporated in vacuo affording 142 mg (55percent) of 2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.1H NMR (400 MHz, CDCl3) delta 2.30-2.68 (m, 4H), 3.62 (m, 1H), 3.74 (m, 1H), 4.00 (m, 2H), 7.75 (m, 2H), 7.88 (m, 2H).To a mixture of 2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione (11.5 g, 44 mmol), tert-butyl cyanoacetate (6.9 g, 49 mmol) and elemental sulfur (1.6 g, 49 mmol) in ethanol (250 ml) was added morpholin (15 ml) and the resulting mixture was stirred at 50¡ã C. for 16 h. The cooled reaction mixture was filtered and the precipitate filtered off and washed with diethyl ether and dried in vacuo affording 6.5 g (35percent) of 2-amino-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.The filtrate was evaporated in vacuo and the residue was dissolved in ethyl acetate (200 ml) washed with water (2.x.100 ml), brine (100 ml), dried (Na2SO4), filtered and the solvent evaporated in vacuo affording 6.0 g (33percent) of almost regioisomer pure 2-amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.2-amino-5-(1,3-dioxo-1,3′-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester1H NMR (300 MHz, CDCl3) delta1.50 (s, 9H), 2.54-2.63 (m, 1H), 2.84-2.90 (m, 1H), 3.79 (q, 1H), 3.96-4.04 (m, 2H), 4.48-4.62 (m, 2H), 5.91 (bs, 2H, NH2), 7.70 (m, 2H), 7.84 (m, 2H).2-amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester1H NMR (300 MHz, CDCl3) delta 1.50 (s, 9H), 2.71-2.90 (m, 2H), 3.67-3.77, (m, 2H), 4.02-4.15 (m, 2H), 4.90 (m, 1H), 6.04 (bs, 2H, NH2), 7.70 (m, 2H), 7.84 (m, 2H).To a solution of 2-amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (6.0 g, 0.014 mol) in ethanol (100 ml) was added hydrazine-hydrate (1.4 ml, 0.029 mol). The mixture was stirred at reflux tem…

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; Novo Nordisk A/S; US7115624; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20876-36-2, 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. 20876-36-2 name is 5-Aminoindolin-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.

Condensation of oxindoles with quinoline-N-oxides: An oxindole (1.6 mmol) may be taken up in acetic anhydride (10 mL) and a solution of quinoline-N-oxide (0.474 mmol) and 5 mL of acetic anhydride may be added. This solution may then be heated at between 0-150¡ãC for between 1-25 hours. In one variation, the reaction is conducted at about 90 ¡ãC for about 3 hours. The resulting solution may then be cooled to room temperature. If a solid is observed upon cooling, the material may be isolated by filtration and washed with a minimal amount of cold MeOH, then dried in vacuo. If no solid is observed upon cooling, the reaction may be diluted with an organic solvent, such as ethyl acetate, washed with brine several times, dried over MgSO4 and concentrated to afford an oil. Purification by preparative HPLC may afford a solid product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; SYRRX, INC.; WO2005/61519; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem