There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 20870-90-0 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 3 h;
N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58percent yield.1H-NMR (300MHz, CDCl3) δ(ppm) : 7.42–7.39 (d, 1H), 7.26 (s, 1H), 6.71–6.68 (d,1H), 3.52–3.20 (s, 2H), 3.19 (s, 3H).
Reference：
[1] European Journal of Organic Chemistry, 2011, # 20-21, p. 3781 - 3793
[2] RSC Advances, 2016, vol. 6, # 74, p. 70221 - 70225
[3] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
[4] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 1,23
2
[ 10075-52-2 ]
[ 20870-90-0 ]
Yield
Reaction Conditions
Operation in experiment
91%
With 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one In 1,4-dioxane; water at 140℃; for 5 h;
Add 0.4 mL of 1,4-dioxane to a 50 mL reaction tube at room temperature.Add 2 mL of water and mix by stirring.Weighing 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one (175 mg, 0.66 mmol) was added to the reaction tube and stirred for 1 min.After the reaction tube was placed in a 140 ° C oil bath, 5-bromo-N-methyl hydrazine (121 mg, 0.6 mmol) was added.A built-in condenser was added and reacted in a 140 ° C oil bath for 5 hours.The TLC dot plate shows that the raw material reaction is complete,Take the reaction tube out of the oil bath.Cool to room temperature,The reaction was quenched by the addition of 10 mL of saturated sodium bicarbonate.It was extracted with ethyl acetate (20 mL).The organic layer is concentrated by steaming,The pale pink solid 5-bromo-N-methyl-substituted 2-indolone 124 mg was obtained by column chromatography, yield 91percent.
Reference：
[1] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1437 - 1442
[2] Patent: CN108129377, 2018, A, . Location in patent: Paragraph 0044-0045
3
[ 87-48-9 ]
[ 74-88-4 ]
[ 20870-90-0 ]
Reference：
[1] Chemistry - An Asian Journal, 2017, vol. 12, # 7, p. 734 - 743
4
[ 2058-72-2 ]
[ 20870-90-0 ]
Reference：
[1] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[2] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2595 - 2598
[3] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
5
[ 87-48-9 ]
[ 20870-90-0 ]
Reference：
[1] Organic Letters, 2015, vol. 17, # 6, p. 1373 - 1376
[2] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2595 - 2598
[3] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
Reference：
[1] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
8
[ 20870-90-0 ]
[ 73183-34-3 ]
[ 1220696-38-7 ]
Yield
Reaction Conditions
Operation in experiment
85%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane at 80℃;
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, 85percent). 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).
With N-Bromosuccinimide; In acetonitrile; at 0 - 20℃; for 3h;
N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58% yield.1H-NMR (300MHz, CDCl3) delta(ppm) : 7.42-7.39 (d, 1H), 7.26 (s, 1H), 6.71-6.68 (d,1H), 3.52-3.20 (s, 2H), 3.19 (s, 3H).
With potassium tert-butylate; In dimethyl sulfoxide;
EXAMPLE 28 Potassium tert-butoxide (1.66 g) was added portionwise to a stirred solution of (2S,4R)-4-hydroxy-4-(2-mercaptothien-4-yl)-2methyltetrahydropyran (3.15 g) in DMSO (25 ml) and the mixture was stirred at ambient temperature for 5 minutes. 5-Bromo-1-methylindolin2-one (3.71 g) and tetrakis(triphenylphosphine)palladium(O) (1.59 g) were added and the mixture was heated to 100 C. for 75 minutes. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and a mixture of ice and water. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p. 40-60 C.) and ethyl acetate as eluent. The material so obtained was further purified by column chromatography using a 5:1 mixture of methylene chloride and acetone as eluent. There was thus obtained (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]tetrahydropyran (2.45 g, 48%), m.p. 125-127 C. (recrystallized from diethyl ether containing a few drops of methylene chloride) and m.p. 129.5-130.5 C. after a further recrystallisation from ethyl acetate; NMR Spectrum: 1.15 (d, 3H), 1.70 (m, 4H), 1.95 (m, 1H), 3.12 (s, 3H), 3.40 (s, 2H), 3.85 (m, 3H), 6.68 (d, 1H), 7.18 (m, 3H), 7.27 (d, 1H).
With triethylamine; benzyl alcohol;PdCl2[dppf]; In tetrahydrofuran; ethyl acetate;
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).
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 115℃; for 0.333333h;
A mixture of <strong>[20870-90-0]5-bromo-1-methyl-2-oxoindoline</strong> (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).
85%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 80℃;
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).
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 18h;
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),
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃;Inert atmosphere;
A mixture of <strong>[20870-90-0]5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one</strong> (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.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃;Inert atmosphere;
General procedure: A mixture of <strong>[20870-90-0]5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one</strong> (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.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; dichloromethane; at 90℃;Inert atmosphere;
Step 1: 1-methyl-5-(4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1, 3-dihydro-2H-indol-2-one A mixture of <strong>[20870-90-0]5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one</strong> (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 then heated at 90 C. overnight. The reaction mixture was cooled to room temperature then concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 25% EtOAc/Hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.2. found 274.1.
With sodium carbonate;bis(triphenylphosphine)palladium(II)-chloride; In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.166667h;Microwave irradiation;
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),
With sodium ethanolate; In ethanol; for 15h;Inert atmosphere; Reflux;
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.
With hydrazine hydrate; In ethanol; water; at 45℃; for 0.166667h;
General procedure: A mixture of substitutedisoindigo (0.2 mmol) and hydrazine hydrate (3 ml) in freshly distilled EtOH(3 ml) was heated at 45 C for 10 min. The solvent and volatiles wereevaporated to afford pure products as white solids which did not need to bespecially purified.
(E)-5-bromo-3-(2-bromobenzylidene)-1-methylindolin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
With piperidine; In ethanol; for 4h;Reflux; Inert atmosphere;
General procedure: To a solution of the corresponding oxindole (1.0 equiv) in EtOH (0.7 M) at room temperature was added sequentially 2-bromobenzaldehyde (1.2 equiv) and piperidine (0.1 equiv). The reaction mixture was heated to reflux and stirred until the starting oxindole was consumed as judged by TLC (ca. ~4 h). The reaction was allowed to cool to room temperature by removal of the oil bath, and then concentrated under reduced pressure. The crude mixture was purified by flash chromatography eluting with hexanes/EtOAc at the indicated ratio to afford the title compound.
3,8,13-tribromo-5,10,15-trimethyl-10,15-dihydro-5H-5,10,15-triazadiindeno[1,2-a;1',2'-c]fluorine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
61%
With trichlorophosphate; for 2h;Reflux;
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).
4-[8-[(3R)-1-ethylpiperidin-3-yl]methoxy}-5-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)imidazo[1,5-a]pyrazin-6-yl]benzonitrile trifluoroacetic acid salt[ No CAS ]
(Z)-5-bromo-3-((4,6-dimethoxypyrimidin-5-yl)methylene)-1-methylindolin-2-one[ No CAS ]
(E)-5-bromo-3-((4,6-dimethoxypyrimidin-5-yl)methylene)-1-methylindolin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hydroxide; for 10h;Reflux;
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.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
