2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one
- Product Name
- 2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one
- CAS No.
- 1313399-38-0
- Chemical Name
- 2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one
- Synonyms
- (2-METHYL-3-OXOISOINDOLIN-5-YL)BORONIC ACID PINACOL ESTER;2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-isoindol-1-one;2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one;2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-one;1H-Isoindol-1-one, 2,3-dihydro-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
- CBNumber
- CB72663789
- Molecular Formula
- C15H20BNO3
- Formula Weight
- 273.14
- MOL File
- 1313399-38-0.mol
2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one Property
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- Appearance
- Off-white to pink Solid
- InChI
- InChI=1S/C15H20BNO3/c1-14(2)15(3,4)20-16(19-14)11-7-6-10-9-17(5)13(18)12(10)8-11/h6-8H,9H2,1-5H3
- InChIKey
- VBWYOZWWAKZWKG-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C=CC(B3OC(C)(C)C(C)(C)O3)=C2)CN1C
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M340743
- Product name
- 2-Methyl-6-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Isoindolin-1-One
- Packaging
- 50mg
- Price
- $155
- Updated
- 2021/12/16
- Product number
- 189808
- Product name
- 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
- Packaging
- 500mg
- Price
- $646
- Updated
- 2021/12/16
- Product number
- 8498DG
- Product name
- 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
- Packaging
- 100mg
- Price
- $224
- Updated
- 2021/12/16
- Product number
- 189808
- Product name
- 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
- Packaging
- 1g
- Price
- $1050
- Updated
- 2021/12/16
- Product number
- 189808
- Product name
- 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
- Packaging
- 5g
- Price
- $3150
- Updated
- 2021/12/16
2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one Chemical Properties,Usage,Production
Synthesis
1254319-51-1
73183-34-3
1313399-38-0
N-methyl-6-bromoisoindolin-1-one (723 mg, 3.41 mmol) and pinacol ester of bisboronic acid (1.04 g, 4.09 mmol) were added with potassium acetate (1.00 g, 10.2 mmol) and PdCl2 (dppf) catalyst (139 mg, 0.17 mmol) and the reaction system was sealed under nitrogen protection. DMSO (15 mL) was added to the reaction mixture and the reaction was stirred at 90 °C for 5 hours. After completion of the reaction, it was cooled to room temperature, the reaction mixture was diluted with water (250 mL) and extracted with dichloromethane (5 x 50 mL). The organic phases were combined, washed sequentially with water (2×100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude product. Purification by silica gel fast column chromatography (eluent 20% THF/dichloromethane) afforded the target product 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one as a crystalline beige solid (262 mg, 28% yield).NMR [400 MHz, (CD3)2SO] δ 7.91 (br s, 1H), 7.85 (dd, J = 7.6, 1.0 Hz, 1H), 7.59 (dd, J = 7.5, 0.6 Hz, 1H), 4.49 (s, 2H), 3.07 (s, 3H), 1.32 (s, 12H). lRMS (APCI+) m/z Calculated value C15H21Br3O3 [M+H]+ 274, measured value 274.
References
[1] Patent: WO2011/75784, 2011, A1. Location in patent: Page/Page column 113-114
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
[3] Patent: WO2017/107089, 2017, A1. Location in patent: Page/Page column 37; 38
2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one Preparation Products And Raw materials
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