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1220696-38-7

1220696-38-7 Structure

1220696-38-7 Structure
IdentificationBack Directory
[Name]

1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
[CAS]

1220696-38-7
[Synonyms]

1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-indol-2-one
2H-Indol-2-one, 1,3-dihydro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
[Molecular Formula]

C15H20BNO3
[MDL Number]

MFCD18383773
[MOL File]

1220696-38-7.mol
[Molecular Weight]

273.14
Chemical PropertiesBack Directory
[Boiling point ]

468.6±45.0 °C(Predicted)
[density ]

1.14±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[pka]

-0.19±0.20(Predicted)
[Appearance]

Light brown to brown Solid
[InChI]

InChI=1S/C15H20BNO3/c1-14(2)15(3,4)20-16(19-14)11-6-7-12-10(8-11)9-13(18)17(12)5/h6-8H,9H2,1-5H3
[InChIKey]

IGFPFGIDECTAJQ-UHFFFAOYSA-N
[SMILES]

N1(C)C2=C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)CC1=O
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one(1220696-38-7)1HNMR
Hazard InformationBack Directory
[Synthesis]

5-Bromo-1-methyl-2-oxoindoline

20870-90-0

Bis(pinacolato)diboron

73183-34-3

1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

1220696-38-7

1. 5-Bromo-1-methyl-2-oxodihydroindole (537 mg, 2.375 mmol), pinacol bis(boronic acid) (987 mg, 3.89 mmol), potassium acetate (636 mg, 6.48 mmol), Pd(dppf)Cl2-CH2Cl2 (88 mg, 0.108 mmol) and 1,2-di-methoxyethane (15.6 mL) were sequentially added to the microwave reaction vial. -dimethoxyethane (15.6 mL). 2. The reaction mixture was stirred at 80 °C overnight. 3. Upon completion of the reaction, the reaction solution was concentrated and the solvent was removed. 4. The crude product was purified by silica gel column chromatography (Biotage system, cyclohexane/ethyl acetate gradient elution) to afford the target compound 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dihydroindol-2-one (500 mg, 85% yield). 5. The structure of the product was confirmed by 1H-1H-1 , 1H-1 ,2,3,2-dihydroxyethylene dimethoxyethane (15.6 mL). 5. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3): δ 7.78 (d, J = 7.7 Hz, 1H), 7.69 (s, 1H), 6.84 (d, J = 7.7 Hz, 1H), 3.52 (s, 2H), 3.24 (s, 3H), 1.36 (s, 12H). 6. LC-MS (ESI, m/z) analysis showed Rt = 2.90 min, [M-H]- m/z = 274 (HPLC method E).

[References]

[1] Patent: WO2015/144290, 2015, A1. Location in patent: Page/Page column 94
[2] Patent: WO2010/130794, 2010, A1. Location in patent: Page/Page column 54; 55
[3] Patent: US2016/9720, 2016, A1. Location in patent: Paragraph 0589
[4] Patent: US2016/9712, 2016, A1. Location in patent: Paragraph 0365
[5] Patent: US2016/289238, 2016, A1. Location in patent: Paragraph 0318; 0319
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