Author: tianli

These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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 5-Bromoisoindolin-1-one

5-bromoisoindolin-1-one (1.00 g; 4.63 mmol; 1.00 eq) dissolved in a mixture of THF (25.00 ml) and DMF (4.50 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 185 mg; 4.62 mmol; 1.00 eq) and tetrabutylammonium iodide (349.0 mg; 0.92 mmol; 0.20 eq) in THF (23.00 ml). After 1.5 h stirring at rt, 4-methoxybenzyl chloride (724.0 mg; 4.63 mmol; 1.00 eq) was added and the mixture was stirred 18h at rt. The reaction mixture was used in the next step without work-up.

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

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Reference of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3-OBoc-oxindoles 3a and 3e-g were synthesized by following our earlier reportedproceudure.1 In a 100ml round bottom flask was charged with 1g of N-protected isatin, 1equivalent of CeCl3.7H2O and the mixture was dissolved by methanol (2mL/mmol) then0.5equivalent of NaBH4 was added portion wise at 0 C. After addition of NaBH4 the reactionmixture was quenched imidiately by excess of ice and taken extract with ethylacetate twice. Theorganic fractions was combined and dried over anhydrous Na2SO4 and evaporated through rotary vacuum.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jayakumar, Samydurai; Kumarswamyreddy, Nandarapu; Prakash, Muthuraj; Kesavan, Venkitasamy; Organic Letters; vol. 17; 5; (2015); p. 1066 – 1069;,
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Reference of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

(B) 15gm (0.0617mole) 4-phthalimido cyclohexanone was dissolve in 150ml Ethylacetate. Cool the mass to 0C. Add Br2 solution (9.8gm Bra in 25ml of methanol) and0.25gm of Aids under stirring. Stop stirring and allow initiating bromination and findingclear solution then add remaining quantity of Br2 solution and stir for 10-15mins. Washthe reaction mass with 75ml 2% NaS2O3 solution then wash organic phase with 75ml8%NaHCO3. Then in last wash it with brine solution. Collect organic masses andevaporate it under vacuum. Dry it at 50C for 2-3hrs.YIELD: 15gms(75.2%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
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Related Products of 603-62-3, 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 603-62-3 as follows.

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
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Adding a certain compound to certain chemical reactions, such as: 17564-64-6, name is 2-(Chloromethyl)isoindoline-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 17564-64-6, COA of Formula: C9H6ClNO2

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. 7.1.56 2-((2-(2-(Pentan-3-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (4C) White powder, mp 155-156 C, 89% yield; 1H NMR (400 MHz, CDCl3): delta 0.87-0.91 (t, 3H, CH3), 1.09-1.12 (t, 3H, CH3), 2.28-2.34 (q, 2H, CH2), 2.38-2.44 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.74-7.76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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; 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;,
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Application of 3339-73-9,Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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.

EDCHCI (2.8 g, 15.0 mmol) was added to a solution of 3-(1,3-dioxoisoindolin-2-yl)propanoic acid (2.2 g, 10.0 mmol) in THF (30 mL followed by HOBt (1.84 g, 12.0 mmol) and the reaction mixture was stirred for 20 mm at room temperature. 2-methoxyacetohydrazide (1.05 g, 10.0 mmol) was added to the reaction mixture followed by DIPEA (6.4 g, 50.0 mmol) and thereaction mixture was stirred at room temperature for 16 h. Volatiles were removed under reduced pressure and the reaction mixture was diluted with water (30 mL). The aq. layer wasextracted with DCM (3 x 25 mL), combined organic layer was washed with aqueous NaHCO3 solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the product (2.0 g, 65 %) as white solid. ?H NIvIR (400 MHz, DMSO-d6): 6 9.91 (s, 1H), 9.72 (s, IH), 7.88-7.82 (m, 4H), 3.88 (s, 2H), 3.78 (t, J= 7.6 Hz, 2H), 3.30 (s, 3H), 2.25 (t, J?7.6 Hz, 2H); LC-MS: [M+Hj = 306.3 mlz.

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

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (89 pag.)WO2016/105477; (2016); A1;,
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These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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. COA of Formula: C8H4BrNO2

5-bromoisoindole-1,3-dione (10 g, 44.2 mmol) was added to THF (50 mL). The temperature was raised to 80 C, stirred for 24 h, ice water bath, methanol (30 mL) was added dropwise, 3N hydrochloric acid (30 mL), refluxed for 4 h, concentrated, diluted with water (100 mL), then washed with diethyl ether (50 mL ¡Á 2), water phase The mixture was adjusted to pH = 10 with saturated aqueous sodium carbonate, and extracted with EA (50mL¡Á2), dried and concentrated to give 5.7 g (64.1%) of yellow oil.

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

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Liu Zhanzhu; Shen Zhufang; Sun Zhaozhu; Pan Xuan; Zhou Tian; Huan Yi; Guan Baohe; (76 pag.)CN110294744; (2019); A;,
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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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

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; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Recommanded Product: 102359-00-2

Example 38 COMPOUND IN-030 3-[5-(2-Morpholin-4-yl-ethoxy)-1H-indol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-5-carboxylic acid was condensed with 5-(2-morpholin-4-yl-ethoxy)-1HH-indole-2-carbaldehyde to give the title compound.

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

Reference:
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); A1;,
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Electric Literature of 3783-77-5, The chemical industry reduces the impact on the environment during synthesis 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of tert-butyl [(2R)-l-(aminooxy)-3-methylbutan-2-yl]carbamate (5.0 gm, 23.04 mmol) in pyridine (50 ml) was added N-(3-oxo-butyl)-pthalamide (5.0 gm, 23.04 mmol) under stirring at 30C. The reaction mixture was stirred at 30C for 12 hours. After completion of the reaction, solvent was evaporated under vacuum and the residue obtained was dissolved in ethyl acetate (200 ml). The ethyl acetate layer was washed with saturated aqueous ammonium chloride solution, water and brine solution. Layers were separated and organic layer was dried over sodium sulphate. Evaporation of solvent provided crude mass, which was purified by triturating with diethyl ether to provide 6.1 gm of 2-[(3E/Z)-3-({ [(2R)- 2-(tert-butoxycarbonyl)amino-3-methylbutyl]oxy}imino)butyl]-lH-isoindole-l,3(2H)-dione as a colourless oil (63% yield). Analysis: Mass (M+l): ES: 418.3 for C22H31N3O5; 1H NMR (400 MHz, CDC13): delta 7.83-7.88 (m, 2H), 7.70-7.73 (m, 2H), 4.67-4.70 (br s, 1H), 3.84-3.98 (m, 2H), 2.65-2.89 (m, 2H), 2.53 (ddd, 1H), 1.91 (d, 3H), 1.70-1.77 (m, 1H), 1.43 (s, 9H), 0.84-0.90 (m, 6H).

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, 2-(3-Oxobutyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WOCKHARDT LIMITED; CHAVAN, Vijay Prakash; BHAVSAR, Satish; PAVASE, Laxmikant; GUPTA, Sunil; MISHRA, Amit; KALE, Rajesh; JOSHI, Sanjeev; DABHADE, Sanjay Kisan; JADHAV, Sunil Bhaginath; KAYASTHA, Abhijeet Kantilal; PAWAR, Shivaji Sampatrao; RANE, Vipul Prabhakar; AHIRRAO, Vinod Kashinath; YEOLE, Ravindra Dattatraya; DESHPANDE, Prasad Keshav; BHAGWAT, Sachin Subhash; PATEL, Mahesh Vithalbhai; (50 pag.)WO2018/203197; (2018); A1;,
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