Category: 20870-90-0

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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8BrNO

General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.

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; Zhang, Ji-Quan; Li, Shu-Min; Wu, Chun-Feng; Wang, Xing-Lan; Wu, Ting-Ting; Du, Yao; Yang, Yuan-Yong; Fan, Ling-Ling; Dong, Yong-Xi; Wang, Jian-Ta; Tang, Lei; Catalysis Communications; vol. 138; (2020);,
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Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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.

To a solution of 5-fluoropyridine-3-boroniotac acid (CASNo. 872041-86-6, 80mg, 0 57mmol) in 1 ,2-dimethoxyethane (0 7 mL) was added water (0.3 mL) and ethanol (0,2 mL). The solution was then charged with sodium carbonate (60 mg, 0.57mmol), 5-bromo-1-methyl- 1 ,3-dihydro-mdol-2-one (CASNo. 20870-90-0, 132 mg, 0.57 mrnol), and diotachlorobis(triphenylphosphiotane)palladium (II) (CASNo. 13965-03-2, 20.3 mg, 0 029 mmol) The reaction vessel was sealed and is heated by microwave irradiation at 150 C for 10 minutes. The reaction mixture was cooled to room temperature, filtered and concentrated. The resulting residue was partially punfied by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/ 0.1% TFA) Final purification was accomplished via silica gel flash chromatography (methanol-dichloromethane. 0 to 7%) to afford 5-(5-fluoro-pyriotadin-3-yl)-1-methyl-1 3-dihydro-iotandol-2-one; MS. (ES+) m/z 243 (M+Hr; 1H NMR (400 MHz, DMSO-Cf6) delta ppm 3 18 (s, 3 H) 3,64 (s, 2 H), 7 13 (d, J-7.% Hz1 1 H), 7,73 – 7 77 (m, 2 H)1 8.03 (d, J=9 7 Hz, 1 H), 8 53 (d, J=2 7 Hz, 1 H), 8.79 (s, 1 H),

The synthetic route of 20870-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Indoline | C8H9N – PubChem

Related Products of 20870-90-0, The chemical industry reduces the impact on the environment during synthesis 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, I believe this compound will play a more active role in future production and life.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3¡Á30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% 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, 5-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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Indoline | C8H9N – PubChem

Synthetic Route of 20870-90-0, 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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under N2, sodium ( 0.5 g ) was reacted with 30 ml ethanol. When the solution was clear,2.9 g N-Me oxindole was added followed by 3.1 g diethyl carbonate and the resulting reactionmixture was refluxed for 15 hours. Then cooled to room temperature and added to 3Nhydrochloric acid solution ( pH = 2 ). The resulting solution was extracted with ether for threeEntry Catalyst time (h) yieldb(%) drc eed(%)1 3e 5 96 72:28 38e/382 3f 8 96 74:26 21e/33 3g 2 99 73:27 11e/334 3h 8 96 71:29 6e/335 3i 2 95 59:41 1e/26 3j 10 94 68:31 44/1e7 3k 2 93 67:33 1/18 3l 72 61 69:31 8/1times. The organic extracts were combined and dried over magnesium sulfate. Thenconcentrated in vacuo and washed with petroleum ether to give 2.7 g2-oxindole-3-carboxylates 1a (61%) as light yellow 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-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Jing; Jia, Li-Na; Peng, Lin; Wang, Qi-Lin; Tian, Fang; Xu, Xiao-Ying; Wang, Li-Xin; Tetrahedron; vol. 70; 21; (2014); p. 3478 – 3484;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 20870-90-0 as follows. HPLC of Formula: C9H8BrNO

A mixture of 5-bromo-1-methyl-2-oxoindoline (500 mg, 2.212 mmol), Bis(pinacolato)diboron (730 mg, 2.88 mmol), KOAc (651 mg, 6.64 mmol) and PdCl2(dppf).CH2CI2 complex (81 mg, 0.1 1 1 mmol) in Dioxane (8.32 mL) was stirred at 1 15C for 20 min. The reaction mixture was cooled down to RT, filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. EtOAc and saturated aqueous NaHC03 solution were added and both phases were separated. The organic phase was washed twice with brine, dried over MgS04, filtered and concentrated under reduced pressure to afford the title product (1.04 g, 2.208 mmol, quantitative yield) as brown solid. Rt = 1.917 min (LC-MS); ESI-MS = 274.1 [M+1]+ (LC-MS).

According to the analysis of related databases, 20870-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-90-0, 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. 20870-90-0 name is 5-Bromo-1-methyl-2-oxoindoline, 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.

11. Preparation of I -methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one 5-Bromo-1-methylindolin-2-one (537 mg, 2.375 mmol),bis(pmnacolate)diborane (987 mg, 3.89 mmol), potassium acetate (636mg, 6.48 mmol) and Pd(dppf)C12.CH2CI2 (88 mg, 0.108 mmol) wereloaded in a microwave vial and DME (15.6 ml) was added. The reaction mixture was heated at 80 C overnight and was then concentrated. The crude was purified by chromatography on silica gel (biotage, CyHex/EtOAc) to give the product(500 mg, 85%). 1H-NMR (500 MHz, CDCI3) ppm = 7.78 (d, J=7.7, IH), 7.69 (s, IH), 6.84 (d, J7.7, IH), 3.52 (s, 2H), 3.24 (s, 3H), 1.36 (s, 12H). LC – MS (ESI, m/z) Rt = 2.90 mm- 274 (M-?-H) (HPLC method E).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-2-oxoindoline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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-Bromo-1-methyl-2-oxoindoline

EXAMPLE 59A benzyl 1-methyl-oxindole-5-carboxylate A solution of 5-bromo-1-methyl oxindole (3.75 g, 16.6 mmol) and triethylamine (3.48 mL) in THF (40 mL) was treated with benzyl alcohol (2.58 mL) and PdCl2(dppf) (300 mg), stirred under carbon monoxide (680 psi) at 130 C. for 16 hours, depressurized, filtered through diatomaceous earth (Celite), and concentrated. The concentrate was purified on silica gel with 30% ethyl acetate/hexanes to provide 2.36 g of the desired product. MS (ESI(+)) m/z 299 (M+NH4)+; 1H NMR (CDCl3) delta 8.10-8.07 (m, 1H), 7.95 (s, 1H), 7.47-7.33 (m, 5H), 6.86 (d, J=8.1 Hz, 2H), 5.35 (s, 2H), 3.56 (s, 2H), 3.25 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-90-0, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6228868; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-1-methyl-2-oxoindoline

General procedure: General Procedure: Under nitrogen atmosphere, to a stirred solution of N-substituted-2-oxindole (10 mmol) in dry Et2O (40 mL) was added LiHMDS (1.0 M in THF solution, 12 mmol, 12 mL) dropwise at 0 C. The solution was allowed to warm to ambient temperature and stirred for 1 h. Then the solution was cooled to 0 C and TMSCl (13 mmol, 1.6 mL) was added dropwise. The solution was allowed to warm to ambient temperature and stirred for another 3 h. The solvent was removed under reduced pressure, and dry MeCN (40 mL) was charged to the flask. The solution was cooled to 0 C again and Selectfluor (12 mmol, 4.3 g) was added to the solution in small portions. The resulting suspension was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by the addition of water (20 mL) and EtOAc (20 mL). The reaction mixture was extracted with EtOAc (20 mL ¡Á 2). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure Purification of the crude product was performed by flash column chromatography (Hexane/EtOAc) to afford 3-fluorooxindole.

The synthetic route of 20870-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

20870-90-0, Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0.

A mixture of 5-bromo-N-methyloxindole(5 g, 22 mmol) and POCl3 (40 mL) was stirred and refluxed for 2h. After cooling, themixture was poured into ice water, and then extracted with dichloromethane (MC) forthree times. The combined organic layers were dried over anhydrous magnesium sulfate,filtered, and concentrated. The solid was washed with MC, white solid NMT (2.6 g) wasprepared. Yield was 61%.1H-NMR (300MHz, THF) delta(ppm) : 8.58 (s, 3H), 7.63-7.60 (d, 3H), 7.57-7.53 (d, 3H),4.40 (s, 9H).

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-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem