Tag: M.W=100-200

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 480-91-1 as follows. name: Isoindolin-1-one

A mixture of isoindolin-1-one (150 mg, 1.13 mmol), 1D (300 mg, 1.13 mmol), Pd2(dba)3 (31 mg, 0.034 mmol), Xantphos (20 mg, 0.034 mmol) and Cs2CO3 (443 mg, 1.36 mmol) in dioxane (25 mE) was heated to 100 C. for 16 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, filtered and the resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (1-5% MeOH in DCM) to afford compound 1 (270 mg, 75% yield) as an off-white solid: ?H NMR (400 MHz DMSO-d5) oe 8.71 (s, 1H), 8.64 (d, J=8.4 Hz, 1H), 8.07 (t, J=8 Hz, 1H), 7.88-7.83 (m, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59-7.53 (m, 1H), 5.18 (s, 2H), 4.12-4.07 (m, 1H), 1.14-1.09 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 318.1[M+1].

According to the analysis of related databases, 480-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-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. Quality Control of 5-Methoxyindolin-2-one

B. (E)-3-((3-(4-((dimethylamino)methyl)styryl)-l-((2-(trimethylsilyl)indazol-6-yl)methylene)-5-methoxyindolin-2-one[00108] Piperidine (0.01 mL, 0.1 mmol) was added to a solution of 5-methoxyoxindole (52 mg, 0.32 mmol) and (E)-3-(4-((dimethylamino)methyl)styryl)-l-((2- (trimethylsilyl)ethoxy)-methyl)-lH-indazole-6-carbaldehyde (contaminated with TBAF from previous deprotection attempt, 95.5 mg, 0.22 mmol) in EtOH (5 mL). The reaction was then heated to 75C for 25 hrs. The solvent was evaporated in vacuo. Chromatography (5g silica SPE tube, Silicycle, 5-10% MeOH in CH2C12) gave a brown oil (105 mg, contained product and TBAF by NMR). The residue was dissolved in EtOAc (100 mL) and washed with brine (3 x 15 mL), dried over Na2S04 and the solvent was evaporated in vacuo to give the title compound as a brown oil (1 lOmg, used without further purification).

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
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Synthetic Route of 2058-74-4, The chemical industry reduces the impact on the environment during synthesis 2058-74-4, name is 1-Methylisatin, I believe this compound will play a more active role in future production and life.

General procedure: The dicationic ionic liquid 10 (27.03 mg, 10 mol %), was added to a mixture of 1,3-dicarbonyl (1 mmol), isatin (1 mmol), malononitrile (1 mmol), and K2CO3 (13.8 mg, 10 mol %) in water (3 mL). The reaction mixture was stirred at reflux for the appropriate time. After reaction completion (TLC), the reaction mixture was cooled to room temperature and filtered. The filtrate was washed with cool ethanol (3 ¡Á 5 mL) to obtain the corresponding 4H-pyran. The crude products were purified by recrystallization from ethanol (95%). To recover 10, the ethanol/water phase was evaporated under reduced pressure and the crude was washed with ethyl acetate (3 ¡Á 5 mL) and air dried.

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, 1-Methylisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Niknam, Khodabakhsh; Khataminejad, Mohsen; Zeyaei, Fariba; Tetrahedron Letters; vol. 57; 3; (2016); p. 361 – 365;,
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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. 150560-58-0, name is 5-Isopropylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Isopropylindoline-2,3-dione

General procedure: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL¡Á4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

According to the analysis of related databases, 150560-58-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
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60434-13-1, name is 5-Chloro-1-methylindoline-2,3-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. Safety of 5-Chloro-1-methylindoline-2,3-dione

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
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7699-18-5, name is 5-Methoxyindolin-2-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. Formula: C9H9NO2

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methoxy-3-(propan-2-ylidene)indolin-2-one (7g): Prepared from 5-methoxy-2-oxindole according to RP 1 on a938 mmol scale. The title compound (176 mg, 866 mmol, 92 %) was obtained as a yellow solid. RF 0.45 (P/EA1 : 1; UV). numax(ATR)/cm1 3150w, 3030w, 2938w, 2836w, 1694vs (CO),1619s, 1594w, 1479s, 1305m, 1203w. deltaH (CDCl3, 250 MHz,300 K) 8.07 (1H, s, NH), 7.14 (1H, d, 4J 1.6, H-4), 6.78-6.72(2H, m, H-6/H-7), 3.81 (3H, s, OCH3), 2.62 (3H, s, H-3′), 2.36(3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K) 169.8 (s, C-2), 156.0(s, C-3′), 155.2 (s, C-5), 133.4 (s, C-7a), 125.6 (s, C-3a), 123.4 (s,C-3), 111.9 (d, C-4), 111.8 (d, C-6), 109.3 (d, C-7), 56.1 (q,OCH3), 25.3 (q, C-1′), 23.3 (q, C-30). m/z (HRMS ESI)204.1019; [M H)](C12H13NO2) requires 204.1019.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
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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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 59-48-3

5-(Bromo)-1,3-dihydro-indol-2-one A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96 %) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
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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.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

Statistics shows that 2-Oxoindoline-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 102359-00-2.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Recommanded Product: 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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Application of 774-47-0, 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. 774-47-0 name is 5,6-Difluoroindoline-2,3-dione, 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.

General procedure: To a stirred solution of potassium hydroxide (5 equiv.) in water (4 mL/g) in an ice-water bathwas added the isatin (1 equiv.) portionwise. The reaction mixture was stirred at roomtemperature for 10 minutes, then cooled in an ice-water bath and acetone (4 mL/g) wasadded dropwise. The reaction mixture was stirred in a 70 C heating block for the specifiedtime, then was cooled in an ice-water bath and a solution of aqueous 5 M hydrochloric acidwas added dropwise until the mixture reached pH 5-6. The reaction mixture was stirred atroom temperature for 10 minutes and then filtered. The resultant solid was filtered, driedand purified as specified

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Difluoroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lindsay-Scott, Peter J.; Barlow, Helen; Synlett; vol. 27; 10; (2016); p. 1516 – 1520;,
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