Author: tianli

603-62-3, These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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.

Example 29 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(4-(methylsulfonamido)-1 ,3-dioxoisoindolin-2-yl)acetoxy)- ethyl)pyridine 1 -oxide (Compound 162) Scheme 29 Step 1 : Preparation of tert-butyl 2-(4-nitro-1 ,3-dioxoisoindolin-2- yl)acetate (157) To a solution of 3-nitrophthalimide (1 g, 5.20 mmol) in dry DMF (35 ml), cooled in an ice bath, NaH (60% w/w dispersion in mineral oil, 0.250 g, 6.25 mmol) was added, followed after 15 minutes by t-butyl bromoacetate (0.845 ml, 5.73 mmol). After stirring for 1 hour at room temperature, the mixture was poured into water and the resulting precipitate was washed with water and with a little amount of Et20; after drying, tert-butyl 2-(4-nitro-1 ,3-dioxoisoindolin-2-yl)acetate was obtained (1 .44 g, 4.70 mmol, 90% yield, MS/ESI+ 328.9 [MNa] +).

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 603-62-3.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); A2;,
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100487-74-9, The chemical industry reduces the impact on the environment during synthesis 100487-74-9, name is 6-Chloro-5-fluoroindolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A reaction mixture of the proper substituted indolin-2-ones 6,aldehyde (1.2 eq.), and piperidine (0.1 eq.) in ethanol (1 mL/0.5 mmol oxindole) was refluxed for 3-5 h, under nitrogen atmosphere. After, the mixture was cooled and put on ice, where the product precipitated. The product was filtered in vacuum with cold ethanol [10,14-17]. Finally, the product was placed in the vacuum desiccators to give the expected compound. The indolin-2-ones 3e was generated through substituted isatin in the presence of hydrazine monohydrate and ethylene glycerol, under reflux [18].

The chemical industry reduces the impact on the environment during synthesis 6-Chloro-5-fluoroindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nunes, Rute C.; Ribeiro, Carlos J.A.; Monteiro, Angelo; Rodrigues, Cecilia M.P.; Amaral, Joana D.; Santos, Maria M.M.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 168 – 179;,
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2058-72-2, Adding some certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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 2058-72-2.

To a stirred mixture of isocyanoacetate 1 (0.12 mmol),2-MeOC6H4CO2H (10 mol%), 4a (10 mol%), and AgPF6 (11 mol%)in THF (0.5 mL) was added isatin 2 (0.1 mmol) and THF (0.5 mL)at 0 C. The reaction was then allowed to proceed at 0 C for 4-6h. Upon completion, the reaction mixture was purified by flashchromatography on silica gel to afford the desired product.Analytical data of some typical compounds:

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; Lu, Yan; Wang, Min; Zhao, Xiaohu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Synlett; vol. 26; 11; (2015); p. 1545 – 1548;,
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Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, 317-20-4

In a 25 ml round bottom flask were added N, N’-dibutyl-2-nitroethylene-1,1-diamine (1 mmol) and 7-Indoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mmol) were added under heating with magnetic stirringTo 110 C for 14 hours. The reaction was monitored by TLC, until the point of complete disappearance of raw materials, the reaction was added 50 ml of acetic acidEster and 50 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous Na 2 SO 4. The dried organicThe phase was concentrated to dryness decompression pressure, after adding 3 ml of concentrated dry distillate acetone and 4 grams of 100 ~ 200 mesh silica gel Stirred byDrying under pressure, loading the sample, separating and drying on a silica gel column using a petroleum ether / ethyl acetate = 7: 1 eluent to obtain a red solid product N-butyl-2- (Butylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (Compound 32) in 90% yield.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
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675109-26-9, A common compound: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10% acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80%). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J- 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

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, 6-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
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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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 3484-35-3

General procedure: To a mixture of oxindole (3a-f, 0.3mmol), 1-alkyl-1H benzo[d]imidazole-2-carbaldehydes (7a-e, 0.33mmol) in ethanol (2mL), was added catalytic amount of piperidine. The reaction mixture was stirred at reflux until complete consumption of the oxindole observed by TLC. After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-ones 8a-z orange/yellow solids in moderate to good yields. Compounds 8c, 8f, 8i, 8l and 8o did not precipitated out from ethanol, were purified by column chromatography with silica gel (60-120) by using ethyl acetate:hexane (2:8 to 3:7). 4.1.1.14 (E)-3-((1-Ethyl-1H-benzo[d]imidazol-2-yl)methylene)-5-methylindolin-2-one (8n) Orange solid, Yield 84%; mp: 274-276 C; FT-IR: (cm-1): 3166, 3067, 2980, 1704, 1615, 1323, 813, 742;1H NMR (300 MHz, DMSO-d6): delta 10.20 (brs, 1H, NH), 9.22 (s, 1H, Ar-H), 7.87 (d, J = 7.2 Hz, 1H, Ar-H), 7.65-7.58 (m, 1H, Ar-H), 7.56 (s, 1H, C=CH), 7.51-7.28 (m, 2H, Ar-H), 7.09 (d, J = 7.9 Hz, 1H, Ar-H), 6.78 (d, J = 7.9 Hz, 1H, Ar-H), 4.54-4.41 (m, 2H, CH2), 2.38 (s, 3H, CH3), 1.50 (t, J = 7.3 Hz, 3H, CH3); 13C NMR (125 MHz, DMSO-d6): delta 168.9, 146.8, 142.9, 141.3, 134.6, 131.7, 131.2, 129.9, 128.6, 124.1, 122.9, 121.1, 119.8, 117.1, 110.6, 109.3, 38.4, 21.0, 15.7; HRMS (ESI): m/z calcd for C19H18N3O 304.1450, found 304.1438 [M+H]+; Purity: 98.7%.

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; Sharma, Pankaj; Thummuri, Dinesh; Reddy, T. Srinivasa; Senwar, Kishna Ram; Naidu; Srinivasulu, Gannoju; Bharghava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 584 – 600;,
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3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, 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. 3416-57-7

To a mixture of N-acetonylphthalamide 3 (8.8 g, 43.3 mmol) and pyrrole (40 mL) was added TFA (3.2 mL, 43.3 mmol) in one portion. The reaction solution was stirred for 10 h at room temperature. The reaction was quenched by adding triethylamine (5 mL). The residual pyrrole was then removed by evaporation in vacuo. To the resulting brownish sticky oil, CH2Cl2 (150 mL) and 10% aqueous NaOH (100 mL) were added, before the organic layer was separated off and washed three times with 120 mL of water. The organic layer was dried over anhydrous MgSO4 and the solvent was removed invacuo to give a brownish sticky oil. The crude product was purifiedby column chromatography over silica gel (1:1 ethyl acetate: hexanesv/v) to give 6.17 g (44.7% yield) of 4 as a pale yellowish solid: 1H NMR (600 MHz, DMSO-d6) delta 10.39 (s, 2H), 7.80 (s, 4H), 6.60-6.59 (q, 2H, J = 2.4 Hz), 5.85-5.84 (q, 2H, J = 2.4 Hz), 5.79-5.78 (m, 2H), 4.07 (s, 2H), 1.57 (s, 3H); 13C NMR (150 MHz, DMSO-d6) delta 167.6, 135.0, 134.1, 131.5, 122.8, 117.1, 106.3, 104.4, 46.8, 40.5, 24.4. HRMS(ESI): m/z calcd for C19H17N3O2 [M – H]-: 318.1243; found 318.1249.

Statistics shows that 3416-57-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Oxopropyl)isoindoline-1,3-dione.

Reference:
Article; He, Ying-Chun; Ren, Zhen-Xing; Zhao, Xue-Feng; Zhang, Yong-Bin; Wang, Jun-Hong; Chao, Jian-Bin; Wang, Meng-Liang; Tetrahedron; vol. 75; 36; (2019);,
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52351-75-4, The chemical industry reduces the impact on the environment during synthesis 52351-75-4, name is 6-Methoxyindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

5.0 g (1 equivalent) of 6-methoxyisatin was dissolved in 25 ml of ethanol.Add 4 ml (1.1 equivalents) of acetophenone and 5.2 g (3 equivalents) of potassium hydroxide solid, heat at 80 C under reflux, and stir for 48 hours.The heating and stirring were stopped, the ethanol was concentrated to dryness, and extracted with ethyl acetate and water three times. The organic phase was combined, and the organic phase was concentrated by spin-drying, and then neutralized by adding 2N diluted hydrochloric acid in an ice bath to precipitate a solid. After the test paper was detected to be weakly acidic, the acid was stopped to be added dropwise, and the mixture was allowed to stand for filtration, and the filter cake was washed with water to obtain 6.20 g of a pale red solid. The yield was 74%.

The chemical industry reduces the impact on the environment during synthesis 6-Methoxyindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sun Yat-sen University; Wang Yuanxiang; Zhang Xiaolei; Huang Qiuyao; Zhong Yan; Hu Wenhao; (26 pag.)CN110105279; (2019); A;,
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Adding some certain compound to certain chemical reactions, such as: 3335-98-6, name is 1-Phenyloxindole, 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 3335-98-6. 3335-98-6

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

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 1-Phenyloxindole.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
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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 71294-03-6 as follows. 71294-03-6

Example 9 Preparation of 3-(4,6-diethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one 7-Fluoro-1,3-dihydro-2H-indol-2-one (1.0 g) is introduced as initial charge in 10 ml of N,N-dimethylacetamide. A solution of potassium carbonate (1.8 g) and potassium hydroxide (0.3 g) in 10 ml of water is added and the mixture is briefly after-stirred. Then, a solution of 2-chloro-4,6-diethoxy-1,3,5-triazine (3.0 g, ca. 50% purity) in 10 ml of N,N-dimethylacetamide, and 10 ml of water are added. A solid separates out from the clear yellow solution. The mixture is stirred at room temperature and further 2-chloro-4,6-diethoxy-1,3,5-triazine (1 g, ca. 50% purity) is added in two portions after 2 and 18 hours. The mixture is stirred for a further 3 hours at 30 C., admixed with 10 ml of toluene, adjusted to pH 1-2 with hydrochloric acid (10%) and after-stirred for 30 min. The solid is filtered off with suction, washed twice alternately with water and heptane and dried. This gives the title compound as solid in an HPLC purity of 99% area (1.53 g, 72% of theory). LC-MS: M+H=319 (86%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.3 (s, 1H), 7.59 (d, 1H), 6.96 (dd, 1H), 6.93-7.00 (m, 1H), 4.50 (q, 4H), 1.37 (t, 6H).

According to the analysis of related databases, 71294-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Karig, Gunter; Ford, Mark James; Siegel, Konrad; US2013/345422; (2013); A1;,
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