N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)acetamide synthesis
- Product Name:N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)acetamide
- CAS Number:1235450-93-7
- Molecular formula:C15H22BNO3
- Molecular Weight:275.15
![AcetaMide, N-[(4-broMophenyl)Methyl]-](/CAS/GIF/90561-76-5.gif)
90561-76-5
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Yield:1235450-93-7 95%
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in dimethyl sulfoxide at 80; for 3 h;Inert atmosphere;Sealed tube;
Steps:
Tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (15)
General procedure: A sealed tube was charged with 13 (200 mg, 0.7 mmol), bis(neopentylglycolato)diboron (197 mg, 0.77 mmol), AcOK (304 mg, 3.1 mmol), and DMSO (3.5 mL). The resulting suspension was deoxygenated by sparging with nitrogen gas. Pd(dppf)Cl2 (17 mg, 0.021 mmol) was added, and the tube was sealed tightly and heated at 80 °C for 3 h. Water (6 mL) was added, and the mixture was extracted with EtOAc (3 mL × 3), washed with brine (3 mL × 3), and dried over MgSO4. The organic layer was concentrated in a vacuum, and the residue was puried by column chromatography (silica gel, petroleum ether : EtOAc = 5 : 1) to give compound 15 as a white solid (37 mg, 16% yield).
References:
Chen, Caiping;Chen, Hui;Cheng, Keguang;Li, Minglei;Liu, Jun;Liu, Shengjie;Sun, Hongbin;Wang, Yue;Wen, Xiaoan;Xu, Qing-Long;Yuan, Haoliang;Zhou, Jin;Zhou, Shuxi;Zhou, Xinyu [European Journal of Medicinal Chemistry,2020,vol. 199] Location in patent:supporting information
108-24-7
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3959-07-7
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