| 81% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl acetamide at 100℃; for 2h; Inert atmosphere; |
7-3 Preparation 7-1. 4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)-indan-l- one.
General procedure: Preparation 7-1. 4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)-indan-l- one. [00122] To a solution of 4-bromo-l-indanone (1.0 g, 4.74 mmol) in N,N- dimethylacetamide (25 mL) was added bw(pinacolato)diboron (2.41 g, 9.48 mmol), 1,1 '- ^w(diphenylphosphino)ferrocene palladium(II) dichloride (346 mg, 0.47 mmol) and potassium acetate (1.40 g, 14.22 mmol) and the reaction mixture was stirred at 100 °C for 2 h under nitrogen. The mixture was evaporated and the residue was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by column chromatography eluting with hexane: ethyl acetate (100:0->4: 1) to give the title compound (1.8 g, 7.00 mmol, ca. 100%) as an off-white powder. LCMS: 97%, Rt 1.811 , ESMS m/z 259 (M+H-CH4)+. |
| 81% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl acetamide at 100℃; for 2h; Inert atmosphere; |
7-3 Preparation 7-1. 4-(4,4,5,5-Tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-indan- 1-one.
General procedure: To a solution of 4-bromo-l-indanone (1.0 g, 4.74 mmol) in N,Ndimethylacetamide (25 mL) was added bis(pinacolato)diboron (2.41 g, 9.48 mmol), 1,1’-bis(diphenylphosphino)ferrocene palladium(11) dichloride (346 mg, 0.47 mmol) and potassiumacetate (1.40 g, 14.22 mmol) and the reaction mixture was stirred at 100 °C for 2 h undernitrogen. The mixture was evaporated and the residue was diluted with water (50 mL) andextracted with dichloromethane (3 x 50 mL). The combined organic layers were dried oversodium sulfate and evaporated. The residue was purified by column chromatography eluting withhexane:ethyl acetate (100:0-4:1) to give the title compound (1.8 g, 7.00 mmol, Ca. 100%) as anoff-white powder. LCMS: 97%, Rt 1.811, ESMS m/z 259 (M+H-CH4). |
| 81% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl acetamide at 100℃; for 2h; Inert atmosphere; |
7-3 Preparation 7-1. 4-(4,4,5,5-Tetramethyl- 1 ,3,2-dioxaborolan-2-yI)-indan- 1-one.
General procedure: [00116] To a solution of 4-bromo-1-indanone (1.0 g, 4.74 mmol) in N,Ndimethylacetamide (25 mL) was added bis(pinacolato)diboron (2.41 g, 9.48 mmol), 1,1’- bis(diphenylphosphino)ferrocene palladium(II) dichloride (346 mg, 0.47 mmol) and potassium acetate (1.40 g, 14.22 mmol) and the reaction mixture was stirred at 100 °C for 2 h under nitrogen. The mixture was evaporated and the residue was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mE). The combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by column chromatography eluting with hexane:ethyl acetate (100:0-)4:1) to give the title compound (1.8 g, 7.00 mmol, Ca. 100%) as an off-white powder |
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