Author: Jessica.F

Related Products of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

N-(5-bromopentyl)phthalimide (1.2g, 4mmol) and thiomorpholine 1,1-dioxide (1.08g, 80mmol) and DIPEA (2ml, 11mmol) was added 10mL i-PrOH, the temperature was raised to 105 deg. C stirred for 16 hours. LCMS traced the reaction. After completion of the reaction it was concentrated, 50ml of water was added, sonicated, and filtered to give a white solid N-(5-(1,1-dioxothiomorpholin-4-yl)pentyl)phthalimide (1.0g, 97% yield).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; Shenzen Chipscreen Biosciences Ltd.; Lu, Xianping; Liu, Jindi; Yang, Qianjiao; Li, Zhiping; Pan, Desi; Shan, Song; Zhu, Jiangfei; Wang, Xianghui; Liu, Xiangheng; Ning, Zhiqiang; (30 pag.)CN105481778; (2016); A;,
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Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-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.

6-Bromoisoindolin-l-one (CAS 675109-26-9) (1.61 g, 7.58 mmol, 1.05 equiv.) was suspended in 32 ml of THF and cooled to 0-5C. Sodium hydride (60% dispersion in mineral oil) (318 mg, 7.94 mmol, 1.1 equiv.) was added at 0-5C. The reaction mixture was stirred at room temperature for 15 minutes and then cooled to 0-5C. Methyl (2RS)-2-bromo-2-(5-fluoro-2- methoxyphenyl)acetate (CAS 1368458-30-3) (2.00 g, 7.22 mmol) dissolved in 8.0 ml of THF was added dropwise at 0-5C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4CI- solution and extracted with ethyl acetate. The aqueous layer was backextracted with ethyl acetate. The organic layers were washed with water and brine. The organic layers were combined, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with an ethyl acetate:heptane 0: 100 to 50:0 gradient to obtain the desired methyl (2RS)-2-(6-bromo-l-oxo- isoindolin-2-yl)-2-(5-fluoro-2-methoxy-phenyl)acetate (2.202 g, 75 % yield) as a yellow foam, MS: m/e = 408.0/410.0 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; JAESCHKE, Georg; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; DUPLESSIS, Martin; NAGEL, Yvonne Alice; KUHN, Bernd; (60 pag.)WO2018/220149; (2018); A1;,
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Related Products of 18711-13-2, 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 18711-13-2 as follows.

General procedure: Example 1- Synthesi s of 4,7 dichloroisatin analogs [0176] An appropriate acetophenone and 4, 7-dichloroisat were condensed in the presence of a catalytic amount of diethylamme to prepare the desired compound in quantitative yield. Example compounds: R1 = 4′-CN (PT-1-11); 2′-GCH3 (PT-1-12) ; 3′- OCH3 (PT-1 -18) ; 2 FontWeight=”Bold” FontSize=”10″ ,4′-OCH3 (PT-1-19); 2,.3′-( }( 1 i ¡¤. (PT-1-20); 3′,4OCH3 (PT-1 -21 ); 35’OCH3 (PT-1-22); 2,,3′,4′,-OCH3 (PT-1-23); 3’A 5′-OCH3 (PT-1-13); 4′-OC2H5 (PT-1- 14); 4 -CF3 (PT-1-15); 4′-OCF3 (PT-1-16); 4′-N(CH3)2 (PT-1-17); 4′-OPh (PT-1-60); 4′-SCH3 (PT-1-67); and 4′-C(CH3)2 (PT-1-67).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGETOWN UNIVERSITY; TORETSKY, Jeffrey, A.; UREN, Aykut; WO2015/61229; (2015); A1;,
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Synthetic Route of 337536-15-9, The chemical industry reduces the impact on the environment during synthesis 337536-15-9, name is 4-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

The compound II obtained in Example 3 was dissolved in 2 L of THF. Cool down to 0 C, Sodium borohydride 2.5 eq was added in four batches. After the stirring is stable, Add boron trifluoride etherate 2.0 eq, The temperature was further raised to 70 C and refluxed for 8 hours. TLC tracking. Cool down to 0 C, The reaction was quenched by dropwise addition of methanol. Then add 6M hydrochloric acid, Adjust the pH to 3-4, The temperature was further raised to 70 C and refluxed for 8 hours. Cool to room temperature, filter, Mother liquor is concentrated, Get the product hydrochloride.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
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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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

In a microwave vessel, a solution of 5-bromo-l,3-dihydro-isoindole-2-carboxylic acid tert- butyl ester (1.5 equiv.), di(pinacolato)diborane (2.0 equiv.), potassium acetate (2.0 equiv.) in 1,4-dioxane (2.0 mL) is flushed with nitrogen. [l,l’-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 equiv.) was then added and the reaction mixture was flushed again with argon (and heated up to 900C for 20 hours until the reaction is complete on TLC. No purification was carried out.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

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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Related Products of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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Application of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(1, 3-dioxoisoindolin-2-yl) acetaldehyde (4.0 g, 21.15 mmol) in ethanol (40 mL) added hydroxylamine. HC1 (2.930 g, 42.305 mmol), followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at roomtemperature for 16 h. Evaporated off the solvent, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL), followed by brine , dried over sodium sulfate and concentrated under vaccue to give the titled compound (3.2 g, 74percent) as off white solid. LCMS: m/z 204.1 [M+H] ?H NMR (300 MHz, DMSO-d6) 11.36 (s, 1H), 7.98?7.78 (m, 4H), 6.83 (t, J= 3.8 Hz,1H), 4.39 (dd, J= 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110568-64-4, name is 6-Nitroisoindolin-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 110568-64-4, Formula: C8H6N2O3

A mixture of 5-nitro-1 lead noise isobutyl ketone Jie (100mg, 0.56mmoL), reduced iron powder (314mg, 5.6mmoL) was added to ethanol (2. OmL) and concentrated hydrochloric acid (0.5mL) and heated under reflux for 2 hours , TLC the reaction was complete. Cooling, the methanol solution saturated with ammonia (NH3) neutralizing the acid, diatomaceous earth filtration, washed with methanol, the solvent evaporated under reduced pressure to give a white solid 70.0mg, 84% yield

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; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. Application In Synthesis of Potassium 1,3-dioxoisoindolin-2-ide

o a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).1H NMR (400 MHz, CDC13): delta 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

The synthetic route of Potassium 1,3-dioxoisoindolin-2-ide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (244 pag.)WO2018/98208; (2018); A1;,
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Reference of 13861-75-1, 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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, This compound has unique chemical properties. The synthetic route is as follows.

A dried flask under nitrogen was charged with sodium hydride (120 mg, 3.0 mmol) and DMF (1 mL). This rapidly stirred suspension was cooled to 0C using an ice/water bath and spiro[cyclopropane-l,3′-indolin]-2′-one (160 mg, 1.0 mmol, Preparatory Example 4) was added dropwise as a solution in DMF (2 mL). The ice/water bath was removed for 1 minutes before the mixture was recooled to 0C and 2-(chloromethyl)-l- isopentyl-lH-benzo[JJimidazole hydrochloride (236 mg, 1.0 mmol) was added dropwise as a solution in DMF (2.1 mL). The mixture was allowed to warm to rt and stirred there for 16 hours.The mixture was cooled to 0C and ice was added carefully. Partition between EtOAc and water was followed by separation, drying and concentration in vacuo. Preparative HPLC gave isolation of the desired compound, (1 10 mg, 0.31 mmol, 31%). ? NMR (400 MHz): ? 0.96 (d, 6H), 1.45 ( m, 2H), 1.60 (m, 2H), 1.69 (m, IH), 1.82(m, 2H), 4.26 (m, 2H), 5.35 (s, 2H), 6.83 (d, IH), 7.02 (dd, IH), 7.19 (dd, IH), 7.29 (m, 3H), 7.47 (d, IH), 7.81 (m, IH). LC/MS 360 (MH+).

The chemical industry reduces the impact on the environment during synthesis Spiro[cyclopropane-1,3′-indolin]-2′-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; PILKINGTON, Christopher; LUMLEY, James; ANGELL, Richard; MATHEWS, Neil; WO2013/68769; (2013); A1;,
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