Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-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 6941-75-9, Quality Control of 5-Bromoisoindoline-1,3-dione

Phthalimide (leq) was added to a solution of 3-bromomethyl-pyridine (1.1 eq) and K2CO3 (2eq) in DMF under N2. The mixture was stirred at rt for 16 hrs. Reaction was diluted in water and the compound precipitated. The solid was filtered and dried under reduced pressure. Compound was used in the next step without further purification.

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; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
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Reference of 3676-85-5, 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4- aminophthalimide (1 .2 mmol), 2,6-dichlorobenzenesulfonyl chloride (1 .2 mmol), trimethylamine (1.4 mmol), and DMAP (cat.) in toluene was heated at 100 C for 72 h. The reaction mixture wasquenched with H20 and extracted with EtOAc. The combined organic layers was dried overNa2SO4 and filtered. Purification via preparative HPLC gave compound 116 in 3% yield. ?HNIVIR(400 1VIHz, DMSO-d6) 11.75 (s, 1H), 11.22 (s, 1H), 7.74 (d, J= 8.1 Hz, 1H), 7.71 -7.64 (m,2H), 7.59 (dd, J= 8.9, 7.1 Hz, 1H), 7.48 -7.36 (m, 2H). ?3C NIVIR (101 MHz, DMSO) 169.04,169.01, 135.08, 135.04, 134.91, 132.60, 127.08, 125.13, 122.59, 111.35.

The synthetic route of 5-Aminoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7223-50-9, name is N-Propargylphthalimide, 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 7223-50-9, Safety of N-Propargylphthalimide

General procedure: The starting alkyne 1 (0.5 mmol) and dodecane as internal standard(0.22 mmol, 50 muL) were added to a suspension of the Cu-Pd-NPs/MCM-48 catalyst (10 mg) in toluene (5 mL). All reactions werecarried out in a Schlenk-type flask, fitted with a reflux condenser andsealed with a rubber septum. The reaction flask was purged and filledwith H2 (1 atm) through a balloon connected to the flask by a needle,and then heated at 110 ¡ãC. Then, the reaction mixture was centrifugedand the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography(silica gel, hexane/EtOAc). The recovered solid catalyst waswashed with toluene (3 ¡Á 2 mL), dried in an oven, calcined at 150 ¡ãC(4 h), and reduced in H2 atmosphere at 200 ¡ãC before its reuse. The following known compounds included in Table 2 were characterizedby comparison of their chromatographic and spectroscopic data (FTIR,1H NMR, 13C NMR, and MS) with those described in the literature.Styrene (2a)18Yield: 46 mg (0.44 mmol, 89percent); colorless liquid.IR (film): 3082, 3060, 3027, 1630, 1496, 1449, 992, 909, 777, 698 cm?1.1H NMR (300 MHz, CDCl3): delta = 7.35 (m, 2 H), 7.25 (m, 3 H), 6.7 (dd, J =10.8, 17.1 Hz, 1 H), 5.71 (d, J = 17.1 Hz, 1 H), 5.20 (d, J = 10.8 Hz, 1 H).13C NMR (75 MHz, CDCl3): delta = 137.5, 128.5, 127.7, 126.1, 136.9, 113.7.MS: m/z (percent) = 104 (100, [M+]), 103 (40), 78 (35), 77 (17), 51 (17).

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; Buxaderas, Eduardo; Volpe, Maria Alicia; Radivoy, Gabriel; Synthesis; vol. 51; 6; (2019); p. 1466 – 1472;,
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Related Products of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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 solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added to a solution of 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) in tetrahydrofuran(5mL) under argon atmosphere, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6):delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1535610; (2005); A1;,
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Related Products of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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 30 5-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)thiophene-3-carboxylic acid; To a stirred mixture at 0 C. of 2-(3-hydroxy-propyl)-isoindole-1,3-dione (0.2 g, 0.97 mmol), 0.7 M sodium bromide (0.70 ml, 0.46 mmol), TEMPO (3.0 mg, 0.02 mmol) in dichloromethane (1 ml) was added dropwise a solution of bleach (2.1 ml, 4.9 mmol) and sodium hydrogen carbonate (117 mg, 1.4 mmol). The mixture was stirred at 0 C. for 2 hours after the addition was finished. The mixture was extracted with ethyl acetate (3*20 ml). The combined organic extracts were washed with 10% sodium thiosulphate (3*10 ml), brine (10 ml), dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was washed with ethyl acetate (2*1 ml) affording after drying 161 mg (81%) of 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde as a solid. 1H NMR (400 MHz, CDCl3) delta 9.82 (s, 1H), 7.85 (dd, 2H, J=5.6, 2.8 Hz), 7.73 (dd, 2H, J =5.6, 2.8 Hz), 4.04 (t, 2H, J=7.2 Hz), 2.89 (t, 2H, J=7.2 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Hydroxypropyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Jeppesen, Lone; Andersen, Henrik Sune; Olsen, Ole Hvilsted; Judge, Luke Milburn; Holsworth, Daniel Dale; Bakir, Farid; Axe, Frank Urban; Ge, Yu; US2005/119332; (2005); A1;,
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Related Products of 110568-64-4, A common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-1-one, molecular formula is C8H6N2O3, 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.

Intermediate 2; [00194] A suspension of Intermediate 2B (1.6 g, 8.98 mmol) and Pd/C (0.18 g) in MeOH (100 mL) was stirred under H2 (1 arm) for 4 h. The reaction mixture was filtered and the filter cake was washed with MeOH. The combined filtrates were concentrated in vacuo. The crude solid was triturated with MeOH (10 mL) and dried in vacuo to yield Intermediate 2 (800 mg, 5.40 mmol, 60.1 % yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 4.15 (s, 2 H) 5.26 (s, 2 H) 6.77 (dd, J=8.25, 2.20 Hz, 1 H) 6.80 (s, 1 H) 7.16 (d, J=8.79 Hz, 1 H) 8.29 (s, 1 H). MS (ESI) m/z 149.2 (M+H)+.

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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110568-64-4, name is 6-Nitroisoindolin-1-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. Safety of 6-Nitroisoindolin-1-one

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 percent, 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 percent).

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

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;,
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Synthetic Route of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 stirred solution of 2-oxoindoline-5-carboxylic acid (0.177 g, 1.00 mmol) in DMF (2 mL), were added EDCI.HCl (0.24 g, 1.25 mmol), HOBt (0.168 g, 1.25 mmol) and triethylamine (0.35 mL, 2.5 mmol). The solution was stirred for 10 min at 0oC. tert- Butyl ((2S)-1-(4-(1-aminoethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate (0.25 g, 0.83 mmol) was added and the reaction stirred at rt for 6 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain a crude residue which was purified by column chromatography to afford tert-butyl ((2S)-1-oxo-1-(4-(1-(2-oxoindoline-5-carboxamido)ethyl)piperidin-1- yl)propan-2-yl)carbamate (0.11 g, 28%)

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
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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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O2

l-(teri-Butylsulfinyl)-6-nitroindoline (SG4-017): To a solution of 6-nitroindoline (1.00 g, 6.09 mmol) and pyridine (1.48 mL, 18.27 mmol) in DCM (3 mL) was added a solution of t- butylsulfinyl chloride (0.751 mL, 6.09 mmol) at 0 C under Argon. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with HC1 (1 M aq. solution, 1 x 50 mL), water (1 x 50 mL), and brine (1 x 50 mL). The organic layer was dried ( a2S04) and concentrated under reduced pressure. The resulting residue was triturated using EtOAc/hexanes to provide the title compound as a dark yellow solid (1.252 g, 77%). Mp: 108 C (dec). NMR (400 MHz, CDCh) delta: 7.82 (dd, J= 8.1, 2.1 Hz, 1H), 7.67 (d, J= 2.1 Hz, 1H), 7.25 (d, J= 8.1 Hz, 1H), 4.36 (td, J= 10.5, 6.8 Hz, 1H), 3.60 (td, J = 10.5, 6.8 Hz, 1H), 3.30 (dddd, J= 17.3, 10.5, 6.8, 0.8 Hz, 1H), 3.17 (dddd, J= 17.3, 10.5, 6.8, 0.8 Hz, 1H), 1.34 (s, 9H). HPLC-MS (ESI+): m/z 559.3 [70%, (2M+Na)+], 291.2 [100%, (M+H)+].

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
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Application of 16800-68-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16800-68-3 as follows.

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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