Month: March 2021

Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 23 Synthesis of 2-methyl-7-[1,2-dihydro-5-methyl-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (IV-4) Similar procedure as Example 20, 5-methylindolin-2-one 0.41 g (2.8 mmol) and 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) 0.5 g (2.6 mmol) were reacted for 13 hours at 80 to 90 C., and 0.39 g (46%) of the titled compound as a yellow solid was obtained. 1H-NMR(500 MHz, DMSO-d6) delta 14.66(s, 1H, -NH-1), 12.03(s, 1H, -COOH), 10.82(s, 1H, -NH-1′), 7.46(s, 1H, H-4′), 6.96(d, 1H, J=7.70 Hz, H-6′), 6.80(d, 1H, J=7.75 Hz, H-7′), 3.10(t, 2H, -CH2-4), 2.93(t, 2H, -CH2-6), 2.53(s, 3H, -CH3-2), 2.32(s, 3H, -CH3-5′), 1.95(m, 2H, -CH2-5); ESI-MS: 323.2 [M+H]+; 321.1 [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-Methylindolin-2-one, its application will become more common.

Reference:
Patent; JIANGSU SIMCERE PHARMACEUTICAL R&D CO., LTD.; US2010/160318; (2010); A1;,
Indoline – Wikipedia,
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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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Application of 446292-08-6, These common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-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.

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
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Synthetic Route of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 4-chloroindoline (3 g, 19.53 mmol) in H2O (3 mL) was added 2-hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixturewas diluted with EtOAc and the organic portion washed with H2O, dried over Na2SO4, filtered, andconcentrated. The residue was purified by silica gel column chromatography to give the title compound(3.3 g). LCMS m/z = 192.8 [M+H]+; 1H NMR (400 MHz, CD3OD) delta ppm 3.02 (t, 2H, J = 8.2 Hz), 3.46 (t, 2H, J= 8.2 Hz), 4.28 (s, 2H), 6.60 (d, 1H, J = 2.1 Hz), 6.76 (d, 1H, J = 8.0 Hz), 7.09 (t, 1H, J = 8.0 Hz).

The synthetic route of 4-Chloroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ren, Albert; Zhu, Xiuwen; Feichtinger, Konrad; Lehman, Juerg; Kasem, Michelle; Schrader, Thomas O.; Wong, Amy; Dang, Huong; Le, Minh; Frazer, John; Unett, David J.; Grottick, Andrew J.; Whelan, Kevin T.; Morgan, Michael E.; Sage, Carleton R.; Semple, Graeme; Bioorganic and Medicinal Chemistry Letters; vol. 30; 5; (2020);,
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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. 65826-95-1, name is 5-Methylindoline, A new synthetic method of this compound is introduced below., Product Details of 65826-95-1

250ml four bottle,In a nitrogen atmosphere,Add 0.01mol 3,6-dibromo-9H-carbazole,0.03 mol of compound 5-methyl 2,3-dihydro-1H-indole,0.03mol of sodium tert-butoxide,1¡Á10-4 mol Pd2(dba)3,1¡Á10-4 mol of tri-tert-butylphosphine,150ml toluene, heated at reflux for 24 hours,Sampling point plate, the reaction is complete, natural cooling, filtration, rotary evaporation of the filtrate, silica gel column to obtain intermediate A10, purity 93.50%, yield 63.60%.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Xu Kai; Li Chong; Zhang Xiaoqing; Zhang Zhaochao; (40 pag.)CN107880030; (2018); A;,
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Related Products of 39755-95-8, A common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, molecular formula is C9H7NO3, 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.

The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-Methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflex for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 11 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrszinocmbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid. The 11 g of 2-hydrazinocarbonylmethyl-4-anisidine was refluxed for 1 hour in 20 mL of 1N sodium hydroxide. The mixture was cooled, acidified to pH 2 with concentrated hydrochloric acid and extracted 3 times with 25 mL of ethyl acetate each time. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to give 0.8 g of 5-methoxy-2-oxindole as a yellow solid. The combined yield was 1.5 g or 33%.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Indoline | C8H9N – PubChem

Application of 118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, SDS of cas: 2058-72-2

General procedure: solution of isatin (1a) (0.3 gm, 2.04 mmol),proline (2) (0.234 gm, 2.04 mmol) and methyl vinyl ketone (3) (255 muL, 3.00 mmol) in CH3CNwas heated to 80 C for 2 h. After the completion of starting precursor, the reaction mixture wascooled and solvent was evaporated on rotator evaporator to provide brown solid. The reactionmixture was purified by silica gel chromatography using hexane:ethyl acetate (6:4) as an eluentto provide product (4a) as a white 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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tiwari, Keshri Nath; Pandurang, Taur Prakash; Pant, Suyash; Sreelekha; Synthetic Communications; vol. 48; 7; (2018); p. 802 – 808;,
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Reference of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

(E) -N-Benzyl-2-nitro-N- (p-tolyl) ethane- 1,1-diamine (1 milliliter(1 mmol)) and 7-fluoroindoline-2,3-dione (1 mmol) were added, toluene (15 ml) and trifluoroacetic acidUnder stirring, the mixture was heated to 110 C and refluxed for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solutionExtraction was performed by adding 50 ml of ethyl acetate and 50 ml of saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous Na2SO4,The dried organic phase was concentrated to dryness under reduced pressure, and then 3 ml of acetone and 4 g of 100-200 mesh siliconStir the plastic, vacuum evaporated to dryness, the sample was separated with a petroleum ether / ethyl acetate = 7: 1 eluent silica gel column dried to obtain redN-Benzyl-8-fluoro-3-nitro-2- (p-tolylamino) quinoline-4-carboxamide (Compound 40) was obtained in 65% yield.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
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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. 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, A new synthetic method of this compound is introduced below., Computed Properties of C26H31N3O8

Step S301: In a 500 mL three-necked bottle, respectively add 5.14 g of 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro -7-cyano-1H-indole tartrate, 150mL dichloromethane, 5mL triethylamine, and stir;After stirring and dissolving, 2.18 g of di-tert-butyl dicarbonate was added in portions, and the reaction was stirred at room temperature for 2 h to obtain a reaction solution;Add 100 mL of purified water to the above reaction solution, stir for 10 min, then stand still for layering;Wash the separated organic phase with 100 mL of purified water and 100 mL of saturated sodium chloride, and then dry the organic phase with anhydrous sodium sulfate for 2 h, and then filter to obtain a filtrate;The filtrate was concentrated under reduced pressure to obtain 3.92 g of light yellow oily compound II, which was 5-[(2R)-2-(tert-butoxycarbonyl)aminopropyl]-1-[3-(benzoyloxy ) Propyl]-2,3-dihydro-7-cyano-1H-indole, the yield of which is 84.48%.

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; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd.; Chai Guoju; Zhang Ding; Wu Yanpeng; Li Jing; Ge Zhimin; Dai Xinmin; (17 pag.)CN111116448; (2020); A;,
Indoline – Wikipedia,
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