Tag: M.W=200-300

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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 2058-72-2

General procedure: Isatin (1 mmol), dimedone (280 mg, 2 mmol) and ZnO (0.25 mmol) were taken in the round bottom flask and heated to 100 C for 2 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was suspended in 6 mL (3:3 v/v) chloroform and methanol mixture and the catalyst was filtered through Whatman filter paper. The filtrate was concentrated under reduced pressure and the residue was purified by recrystallization in ethanol solvent. The recovered catalyst dried and used for next cycle.

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:
Article; Kothandapani, Jagatheeswaran; Ganesan, Asaithampi; Mani, Ganesh Kumar; Kulandaisamy, Arockia Jayalatha; Rayappan, John Bosco Balaguru; Selva Ganesan, Subramaniapillai; Tetrahedron Letters; vol. 57; 31; (2016); p. 3472 – 3475;,
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Related Products of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

In a microwave vessel, a solution of 5-bromo-l,3-dihydro-isoindole-2-carboxylic acid tert- butyl ester (1.5 equiv.), di(pinacolato)diborane (2.0 equiv.), potassium acetate (2.0 equiv.) in 1,4-dioxane (2.0 mL) is flushed with nitrogen. [l,l’-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 equiv.) was then added and the reaction mixture was flushed again with argon (and heated up to 900C for 20 hours until the reaction is complete on TLC. No purification was carried out.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
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Synthetic Route of 337536-15-9, The chemical industry reduces the impact on the environment during synthesis 337536-15-9, name is 4-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

The compound II obtained in Example 3 was dissolved in 2 L of THF. Cool down to 0 C, Sodium borohydride 2.5 eq was added in four batches. After the stirring is stable, Add boron trifluoride etherate 2.0 eq, The temperature was further raised to 70 C and refluxed for 8 hours. TLC tracking. Cool down to 0 C, The reaction was quenched by dropwise addition of methanol. Then add 6M hydrochloric acid, Adjust the pH to 3-4, The temperature was further raised to 70 C and refluxed for 8 hours. Cool to room temperature, filter, Mother liquor is concentrated, Get the product hydrochloride.

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

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
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Related Products of 18711-13-2, 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 18711-13-2 as follows.

General procedure: Example 1- Synthesi s of 4,7 dichloroisatin analogs [0176] An appropriate acetophenone and 4, 7-dichloroisat were condensed in the presence of a catalytic amount of diethylamme to prepare the desired compound in quantitative yield. Example compounds: R1 = 4′-CN (PT-1-11); 2′-GCH3 (PT-1-12) ; 3′- OCH3 (PT-1 -18) ; 2 FontWeight=”Bold” FontSize=”10″ ,4′-OCH3 (PT-1-19); 2,.3′-( }( 1 i ¡¤. (PT-1-20); 3′,4OCH3 (PT-1 -21 ); 35’OCH3 (PT-1-22); 2,,3′,4′,-OCH3 (PT-1-23); 3’A 5′-OCH3 (PT-1-13); 4′-OC2H5 (PT-1- 14); 4 -CF3 (PT-1-15); 4′-OCF3 (PT-1-16); 4′-N(CH3)2 (PT-1-17); 4′-OPh (PT-1-60); 4′-SCH3 (PT-1-67); and 4′-C(CH3)2 (PT-1-67).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGETOWN UNIVERSITY; TORETSKY, Jeffrey, A.; UREN, Aykut; WO2015/61229; (2015); A1;,
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Synthetic Route 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.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)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 5332-26-3, Recommanded Product: 5332-26-3

To a solution of N-(bromomethyl)phthalimide (2.0 g, 8.3 mmol) in CH2Cl2 (15 mL) was added sodium azide (1.62 g, 24.9 mmol), tetrabutylammonium iodide (0.10 g, 0.33 mmol) and H2O (3 mL). The reaction mixture was heated at reflux for 24 h. The mixture was cooled at room temperature, CH2Cl2 (5 mL) was added and the organic phase was washed and dried over Na2SO4, the solvent was removed in vacuo and the product was purified by crystallisation to afford a yellow solid (1.6 g, 95%); m.p. 39-40 C (lit. 37-39 C);21 FTIR (ATR, cm-1): 3474, 2962, 2872, 2129, 1776, 1712, 1610; 1H NMR (300 MHz, CDCl3) delta 7.94 (dd, J = 5.5, 3.1 Hz, 2H), 7.80 (dd, J = 5.5, 3.1 Hz, 2H), 5.08 (s, 2H); 13C NMR (75 MHz, CDCl3) delta 167.1 (2 ¡Á C), 134.6 (2 ¡Á CH), 131.7 (2 ¡Á C), 123.9 (2 ¡Á CH), 52.2 (CH2); MS [EI+] m/z (%): 202 [M]+ (5), 173 [M – HN2]+ (10), 161 [C8H5N2O2] (10), 159 [M – HN3]+ (40), 147 [C8H5NO2] (10), 133 [C8H5O2] (60), 104 [C7H4O] (100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Bromomethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lopez-Gonzalez, Ricardo; Bautista-Renedo, Joanatan; Martinez-Otero, Diego; Reyes, Horacio; Gonzalez-Rivas, Nelly; Cuevas-Yanez, Erick; Journal of Chemical Research; vol. 40; 5; (2016); p. 308 – 313;,
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Synthetic Route of 20870-90-0, These common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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.

5-bromo-1-methylindolin-2-one (500 mg, 2.21 mmcl) was dissolved in dry THF (5 mL). The solution was purged with N2 and Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added to the solution. The freshly prepared bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol) was added slowly as a solution in THF (approx. 0.8 M). The resulting mixture was heated at 70C for 1 h30. Partial conversion was obersved by LCMS. The mixture was heated at 70C overnight, no change in profile. Further Pd2(dba)3 (127 mg, 0.14 mmol) and XPhos (132 mg, 0.28 mmol) were added followed by bromo[1-(methoxycarbonyl)cyclopropyl]zinc (6.94 mL, 5.55 mmol). Heating to 70C was continued until almost complete conversion was observed (1h30).The mixture was cooled to rt and was quenched with water and EtOAc. The mixture was filtered through a pad of Celite. After phases separation, the remaining organic layer was dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography eluting with a gradient of Cyclohexane/EtOAc from [100:0] to [65:35]. The product fractions were combined and concentrated to dryness to afford methyl 1-(1- methyl-2-oxo-2,3-dihydro-1 H-indol-5-yl)cyclopropane-1 -carboxylate Ex.75a (99 mg, 18%) as pale orange solid. 1H NMR (300 MHz, DMSO-d6, din ppm): 1.12- 1.16 (m, 2H), 1.44-1.48 (m, 2H), 3.09 (s, 3H), 3.51 (s, 2H), 3.52 (s, 3H), 6.88 (d, 1H, J=8.7Hz), 7.21 (d, 1H, J=1.8Hz), 7.23 (d, 1H, J=1.8Hz).

Statistics shows that 5-Bromo-1-methyl-2-oxoindoline is playing an increasingly important role. we look forward to future research findings about 20870-90-0.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
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Synthetic Route of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: 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%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

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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Application of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A mixture of substituted isatin 1 (0.5 mmol), cyclic 1,3-dicarbonyl 2 (0.55 mmol), 4-hydroxyl coumarin 3 (0.55 mmol) and I2 (0.05 mmol) in DCE (2 mL) was heated at 60 C under atmosphere. The progress was monitored using TLC detection. After completion of the present reaction, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography [eluent, petroleum ether/ethyl acetate 5:1] to afford the desired products 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhang, Min; Yang, Wenbo; Qian, Min; Zhao, Ting; Yang, Liuqing; Zhu, Chunyin; Tetrahedron; vol. 74; 9; (2018); p. 955 – 961;,
Indoline – Wikipedia,
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