Category: 20870-90-0

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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).

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Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
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We’ll be discussing some of the latest developments in chemical about CAS: 20870-90-0. Related Products of 20870-90-0

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 (3×30 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.

We very much hope you enjoy reading the articles and that you will join us to present your own research about 5-Bromo-1-methyl-2-oxoindoline.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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Healthcare careers for chemists are once again largely based in laboratories, although increasingly there is opportunity to work at the point of care, helping with patient investigation., Recommanded Product: 20870-90-0

To a solution of 5-bromo-1-methyl-1 ,3-diotahydro-indol-2-one (CASNo. 20870-90-0, 4.07 g, 18.00 mmol). in DMSO (50 mL) was added biotas(pinaco.ato)diboron (5 03 g, 19.80 mmol), and potassium acetate (5.30 g, 54 0 mmol) Next, [1 , 1 ‘-biotas(diphenylphosphiotano)- ferrocene]-d(chloropalladiotaum(ll) complexed with dichloromethane (CASNo. 72287-26-4, 0 417 g, 0 540 mmol) was added The reaction mixture was degassed by bubbling nitrogen through the solution for 3 minutes The reaction was then heated at 80 C for 18 hr The reaction was then poured into ice-water and extracted three times with diethyl ether, The organic extracts were combined, washed with brine, dned over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, O to 70%) to afford 1-methyl-5-(4,4,5,5- tetramethyl-(1 ,3,2Jdioxaboro.an-2-yl)-1 ,3-diotahydro-indol-2-one, 1H NMR (400 MHz1 CDCI3) delta ppm 1 35 (s, 12 H), 3.23 (s, 3 H), 3.51 (s, 2 H), 6 83 (d, J=7,6 Hz, 1 H), 7.69 (S1 1 H)1 7,77 (d, J= 7 8 Hz, 1 H),

As always, wish you can browse a selection of our May HOT articles below about 5-Bromo-1-methyl-2-oxoindoline.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Application In Synthesis of 5-Bromo-1-methyl-2-oxoindoline, 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.

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;,
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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.

General procedure: A mixture of 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (1 g, 4 mmol) [Maybridge, cat10430564], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (1.7 g, 6.6 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.2 mmol) and potassium acetate (1.3 g, 13 mmol) in 1,4-dioxane (40 mL) was purged with nitrogen and then stirred at 90 C. overnight. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.1. found 274.1.

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; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
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Synthetic Route 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.

General procedure: A solution of compound 1 (0.6 mmol) and compound 2 (0.5 mmol) in 8.0 mLof alcohol 3 in the presence of 1.0 eq NaOH was stirred at reflux for 10h. After the removal of alcohol, purification by flash column chromatography (hexane/EtOAc) was carried out to furnish the corresponding products 4 as an orange solid.

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

Reference:
Article; Liu, Xiong-Li; Feng, Ting-Ting; Wang, Dan-Dan; Liu, Huan-Huan; Yang, Chao; Li, Xiao-Nian; Lin, Bing; Zhao, Zhi; Zhou, Ying; Tetrahedron Letters; vol. 57; 36; (2016); p. 4113 – 4118;,
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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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 20870-90-0

To a solution of 5-bromo-1-methyl-1 ,3-diotahydro-indol-2-one (CASNo. 20870-90-0, 4.07 g, 18.00 mmol). in DMSO (50 mL) was added biotas(pinaco.ato)diboron (5 03 g, 19.80 mmol), and potassium acetate (5.30 g, 54 0 mmol) Next, [1 , 1 ‘-biotas(diphenylphosphiotano)- ferrocene]-d(chloropalladiotaum(ll) complexed with dichloromethane (CASNo. 72287-26-4, 0 417 g, 0 540 mmol) was added The reaction mixture was degassed by bubbling nitrogen through the solution for 3 minutes The reaction was then heated at 80 C for 18 hr The reaction was then poured into ice-water and extracted three times with diethyl ether, The organic extracts were combined, washed with brine, dned over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, O to 70%) to afford 1-methyl-5-(4,4,5,5- tetramethyl-(1 ,3,2Jdioxaboro.an-2-yl)-1 ,3-diotahydro-indol-2-one, 1H NMR (400 MHz1 CDCI3) delta ppm 1 35 (s, 12 H), 3.23 (s, 3 H), 3.51 (s, 2 H), 6 83 (d, J=7,6 Hz, 1 H), 7.69 (S1 1 H)1 7,77 (d, J= 7 8 Hz, 1 H),

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20870-90-0.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); 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 20870-90-0 as follows. Quality Control of 5-Bromo-1-methyl-2-oxoindoline

A mixture of 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (Maybridge, cat No.CC63010, 0.30 g, 1.3 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl](500 mg, 2.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (50 mg, 0.07 mmol) and potassium acetate (390 mg, 4.0 mmol) in 1,4-dioxane (10 mL) was purged with nitrogen and heated at 90 C. overnight. After cooling it was concentrated. The crude material was purified by flash chromatography on a silica gel column eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.2. found 274.1.

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; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
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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.

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

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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Electric Literature 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.

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 (3×30 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.

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