Month: July 2021

Some common heterocyclic compound, 100487-74-9, name is 6-Chloro-5-fluoroindolin-2-one, molecular formula is C8H5ClFNO, 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. name: 6-Chloro-5-fluoroindolin-2-one

EXAMPLE 86a; Preparation of intermediate of E/Z-2-[4-chloro-2-(6-chloro-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-ethyl-butyric acid methyl ester; To the mixture of 6-chloro-5-fluoro-1,3-dihydro-indol-2-one (500 mg, 2.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (844 mg, 2.97 mmol) in methanol (5 mL) was added pyrrolidine (95 mg, 1.35 mmol) dropwise. The mixture was then heated at 70 C. for 1 h. After cooled to room temperature, the mixture was partitioned between EtOAc and diluted HCl solution. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product as a red-yellow solid, which was used for the next step reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 100487-74-9, its application will become more common.

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
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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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Nitroisoindolin-1-one

To a solution of 5-nitro-2,3-dihydro-1H-isoindol-1-one (60 mg, 0.337 mmol) in methanol (20 mL) was added 50 mg of 10% Pd on carbon. The mixture was hydrogenated (with a balloon) for 1 hour. Filtration through Celite followed by concentration led to 38 mg of 5-amino-2,3-dihydro-1H-isoindol-1-one as a tan solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Wyeth; US2010/15141; (2010); A1;,
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Application of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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.

An oven-dried screw cap test tube was charged with a magnetic stir bar, 5-nitroisatin (1; 0.192 g, 1 mmol), malononitrile (2; 0.073 g,1.1 mmol), trisodium citrate dihydrate (0.029 g, 10 mol % as organo catalyst),and EtOH:H2O (1:1 v/v; 4 mL) in a sequential manner; the reaction mixture was then stirred vigorously at room temperature for about 20 min. After that, ethyl acetoacetate (3; 0.130 g, 1 mmol)was added to the stirred reaction mixture, and the stirring was continued for 3 h [15]. The progress of the reaction was monitoredby TLC. On completion of the reaction, a solid mass precipitated out that was filtered off followed by washing with aqueous ethanol to obtain crude product. It was purified just by recrystallization from ethanol without carrying out column chromatography. The structure of ethyl 2′-amino-3′-cyano-6′-methyl-5-nitro-2-oxospiro[indoline-3,4′-pyran]-5′-carboxylate (4) was confirmed by analytical as well as spectral studies including FT-IR, 1H NMR, 13C NMR,and TOF-MS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; Sharma, Sakshi; Brahmachari, Goutam; Banerjee, Bubun; Nurjamal, Khondekar; Kumar, Abhishek; Srivastava, Ambrish Kumar; Misra, Neeraj; Pandey, Sarvesh Kumar; Rajnikant; Gupta, Vivek K.; Journal of Molecular Structure; vol. 1118; (2016); p. 344 – 355;,
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Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-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 89-40-7, Quality Control of 5-Nitroisoindoline-1,3-dione

To a solution of 5-nitro-1H-isoindole-1,3(2H)-dione (1.0 g, 5.2 mmol) in dry THF (15 mL) was added 10% Pd/C (0.2 g). The mixture was hydrogenated at 30-40 psi for 17 h. The catalyst was filtered, and the filtrate was evaporated under vacuo to give 0.5 g (59.3%) of 5-amino-1H-isoindole-1,3(2H)-dione as a yellow colour solid.

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, 5-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
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Application of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of 5-trifluoromethoxyisatin (12A, 0.46g, 2.00mmol) in CH2Cl2 (15mL) was added mCPBA (70% pure, 0.54g, 2.2mmol). The resulting solution was allowed to stir for 30 minutes. A solid precipitate formed and was filtered, rinsed with CH2CI2, and dried to yield compound 12B as a solid (0.39g, 79%).

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, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2009/143049; (2009); A1;,
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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 5428-09-1 as follows. name: 2-Allylisoindoline-1,3-dione

The title compound was prepared by utilising Ni(dppp)Br2 (32 mg,50.0 mumol, 10 mol%), zinc powder (6.6 mg) and zinc iodide (32 mg,100 mumol, 20 mol% each). These materials were suspended in dichloromethane(0.3 mL) then Ph2PH solution (0.125 M in dichloromethane,0.2 mL, 25.0 mumol, 5 mol%) was added. 2-Allylisoindoline-1,3-dione (94 mg, 0.502 mmol, 1.0 equiv) was added at ambient temperatureand the reaction mixture was stirred for 18 h. Workup accordingto the general procedure and purification by flash columnchromatography (n-pentane/tert-butyl methyl ether, 20:1) gave 6d asa single E-isomer. Yield: 80 mg (0.426 mmol, 85%); yellow solid.1H NMR (300 MHz, CDCl3): delta = 7.87-7.83 (m, 2 H), 7.75-7.70 (m, 2 H),6.64-6.53 (m, 2 H), 1.84 (d, J = 5.0 Hz, 3 H).13C NMR (76 MHz, CDCl3): delta = 168.8, 134.4, 131.9, 123.6, 118.5, 118.3,16.4.

According to the analysis of related databases, 5428-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Weber, Felicia; Steinlandt, Philipp S.; Ballmann, Monika; Hilt, Gerhard; Synthesis; vol. 49; 2; (2017); p. 440 – 450;,
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Adding a certain compound to certain chemical reactions, such as: 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-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 1336963-95-1, Computed Properties of C8H3BrFNO2

In a solution of compound 2 (2.80 g, 11.48 mmol) in 50 ml of ethanol,Hydrazine hydrate (85%, 0.5 mL) was added under a nitrogen atmosphere,After refluxing for thirty minutes,There is a yellow product after precipitation by suction after drying,Was dissolved in 50 ml of ethanol,T-BuOK (4.03 g, 35.90 mmol) was added,After refluxing for 2 h, the reaction mixture was poured into water,The pH of the system was adjusted to 2 with hydrochloric acid,After extraction with ethyl acetate,Washed,Saturated salt water washing,After drying, distillation under reduced pressure.After the column by silica gelTo give the title compound 3 (1.49 g, yield 56%).

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; Peking University; Pei, Jian; Lei, Ting; Dou, Jinhu; (29 pag.)CN103804271; (2016); B;,
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Electric Literature of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 271: (S)- l-Oxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)- pyridin-2-yl)methyl)isoindoline-5-carboxamide.Step 1. Methyl l-oxoisoindoline-5-carboxylate.To a 25 mL round bottom flask containing 5-bromo-2,3-dihydro-isoindol- 1-one (500 mg, 2.36 mmol), was added TEA. The resulting mixture was then stirred at 23 C for 2 min. At this time, MeOH (954 mu,, 23.58 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (54.6 mg, 0.094 mmol)(Xantphos) and palladium(II) acetate (10.59 mg, 0.047 mmol) were added to the flask. The reaction mixture was then flushed with argon and then with carbon monoxide. The flask was fitted with a rubber septa and a balloon of carbon monoxide was inserted through septa. The flask was stirred at 70 C overnight under carbon monoxide, allowed to cool, diluted with EtOAc (50 mL) and filtered through Celite eluting with EtOAc (300 mL). The solid remaining on the Celite pad was washed with DCM (200 mL) and DCM/MeOH (10: 1)(150 mL) and the filtrates concentrated to give a pale green solid (800 mg). A portion of this material was taken on to the next reaction with no further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
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Related Products of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

Step A: Preparation of 5-BromoisoindoIine.To a solution of 5-bromoisoindoline-l,3-dione (8.117 g, 35.9 mmol) in THF (10 mL) was added boron trifluoride (8.40 mL, 108 mmol) dropwise. The reaction mixture was heated to reflux. After refluxing temperature was reached, borane tetrahydrofuran complex (144 mL, 144 mmol) was added dropwise and the reaction was stirred at reflux for 16 h. The mixture was cooled to 0 0C, cautiously treated with 3 N HCl (10 mL), and stirred at room temperature for 1 h. The aqueous mixture was washed with EtOAc, and the organic phase was discarded. The aqueous layer was basifed (pH 9-10) and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (4.02 g). LCMS m/z = 198.0 [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 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
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Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Salt (n-Bu4N)2[2-B10H9SH] (0.50g, 0.79mmol), N-(bromomethyl)phthalimide (0.38g, 1.68mmol), and cesium carbonate (0.26g, 0.39mmol) were placed in a 25-ml round-bottom flask and dissolved in 4ml DMF. The solution was heated to 80C in an argon atmosphere for 4h. After cooling to room temperature, a precipitate was removed by filtration and the solvent was distilled off on a rotary evaporator, and the dry residue was resuspended in 15ml of distilled water and allowed to stand in an ultrasonic bath to form a flocculated suspension. The precipitate was filtered off and washed with distilled water (2×10 ml) and ethyl acetate (3×5ml). Yield: 82%. Anal. calc. for C34H57B10N3O4S (%): C, 57.35; H, 8.07; N, 5.90; S, 4.50. Found (%): C, 57.15; H, 8.12; N, 5.81; S, 4.32. (0023) 1H NMR (CD3CN, delta, ppm): 7.79 (m, 8H, Ph), 5.04 (d, 2H, J=13.42, SCHaHb), 4.92 (d, 2H, J=13.42, SCHaHb), 3.09 (m, 8H, n-Bu4N+), 1.61 (m, 8H, n-Bu4N+), 1.34 (m, 8H, n-Bu4N+), 0.96 (t, 12H, n-Bu4N+), 0.60-2.10 (m, 9H, B10H9). (0024) 13C NMR (CD3CN, delta, ppm): 167.6 (CO), 135.8, 132.6, 124.4 (Ph), 59.3 (n-Bu4N+), 49.6 (SCH2), 24.3 (n-Bu4N+), 20.3 (n-Bu4N+), 13.8 (n-Bu4N+). (0025) 11B-{1H} NMR (CD3CN, delta, ppm): 3.5 (d, 1B), -4.4 (d, 1B), -18.2 (s, 1B), -26.5 (d, 5B), -30.1 (d, 2B). (0026) IR (CCl4): 3466,5 3091, 3062, 3027, 2959, 2933,2871, 2520, 2477, 1770, 1711, 1613, 1468, 1423, 1388, 1362, 1320, 1186, 1100, 1087, 1026, 978, 931, 860, 796, 717, 661, 603, 527cm-1.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kubasov; Turishev; Golubev; Bykov, A.Yu.; Zhizhin, K.Yu.; Kuznetsov; Inorganica Chimica Acta; vol. 507; (2020);,
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