Month: April 2021

Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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. SDS of cas: 101207-45-8

A mixture of 2-(4-methylbenzyl)isoindoline-l,3-dione (1 g, 3.8 mmol) and hydrazine hydrate (752 mg, 15 mmol, 730 pL) in MeOH (10 mL) was stirred at 20C for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol (with 5% ammonia in water) = 0:1 to 5:1) to give p-tolylmethanamine (160 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Product Details of 496-12-8

To a solution of isoindoline (335 mg, 2.8 mmol) in DCM (5 ml) is added a 2M solution of trimethylaluminum in toluene (1.4 ml, 2.8mmol) and the resulting solution is allowed to EPO stir at ambient temperature for 30 minutes and is then added to a solution of 2-tert- butoxycarbonylamino-3-(2-chloro-3,4-dimethoxy-phenyl)-propinoic acid methyl ester (520 mg, 1.39 mmol) in DCM (5 ml). The reaction is allowed to stir at ambient temperature for 18 h and carefully quenched with a 10% aqueous solution of citric acid. The resulting biphasic mixture is diluted with DCM (20 ml) and extracted with a saturated solution of Rochelle’s Salt (20 ml). The organic layer is separated, concentrated in vacuo and purified by column chromatography (hexanes-ethyl acetate 15- 60%) resulting in 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4-dimethoxy-phenyl)-l-(l,3-dihydro- isoindol-2-yl)-propan-l-one (300 mg, 47%). 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4- dimethoxy-phenyl)-l-(l,3-dihydro-isoindol-2-yl)-propan-l-one is analyzed by HPLC/Mass Spec.

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6 name is 5-Nitroindoline, 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.

A dry Schlenk tube was charged with Cs2C03 (266 mg, 0.816 mmol). The tube was evacuated for 30 min and then flushed with argon and 9 (150 mg, 0.272 mmol) was added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.003 mmol) and X-Phos (6.5 mg, 0.014 mmol). The mixture was dissolved in dry dioxane (5 mL) and the solution was degassed in an ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol) was added and the mixture was stirred for 53 h at 80C. TLC (petrol ether/EtOAc 3:1 ) and mass spectroscopy indicated the formation of partially deacetylated mannoside during the progress of the reaction. Therefore, dry pyridine (2 mL) and dry acetic anhydride (1 mL) were added 50 h after the reaction started to regain fully protected mannoside. Then EtOAc (30 mL) and satd. aq. NaHC03 solution (50 mL) were added to the reaction mixture. The layers were separated and the organic phase was washed with brine (2 x 50 mL). The aqueous layers were extracted with EtOAc (3 x 30 mL). The combined organic layers were dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified with silica gel chromatography (petrol ether/EtOAc, 10:1 -1 :1 ) to give 10 (128 mg, 80%) as an orange solid.1H NMR (CDCI3): delta 2.02, 2.20 (2s, 12H, 4 OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, Ar), 6.98 (m, 3H, Ar), 7.30 (t, J = 8.1 Hz, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.05 (d, J = 8.8 Hz, 1 H, Ar).

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; UNIVERSITY OF BASEL; ERNST, Beat; WO2012/164074; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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