1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolidine

22090-26-2

73183-34-3

852227-90-8

General procedure for the synthesis of 1-(4-(4-bromophenyl)pyrrolidine and bis(pinacolato)diboron (1.21 g, 4.78 mmol) from 1-(4-bromophenyl)pyrrolidine and pinacolato)diboron (1.21 g, 4.78 mmol) in a flask protected by argon gas containing 1-(4-bromophenyl)pyrrolidine (722 mg, 3.19 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), potassium acetate (939 mg, 9.56 mmol) and PdCl2 (dppf) (79 mg, 0.097 mmol). 4.78 mmol), potassium acetate (939 mg, 9.56 mmol), and PdCl2(dppf) (79 mg, 0.097 mmol) were added to a flask pre-purged with argon (30 mL) of 1,4-dioxane. The reaction mixture was refluxed under argon atmosphere for 14 hours. Upon completion of the reaction, the reaction mixture was extracted with hexane and the organic phases were combined, dried over anhydrous sodium sulfate and filtered. Purification by silica gel column chromatography (eluent: hexane/ethyl acetate = 17:3) gave a black needle-like target product (575 mg, 2.10 mmol, 66% yield). Thin layer chromatography (TLC, silica gel plate, unfolding agent: chloroform) showed Rf = 0.60.1H NMR (CDCl3) data: δ = 1.32 (12H, s), 1.92-2.1 (4H, m), 3.23-3.4 (4H, m), 6.53 (2H, dd, J = 6.5, 1.8 Hz), 7.67 (2H, dd, J = 6.5, 1.8 Hz). 1.8 Hz).APCI-MS (CHCl3) analysis: m/z calculated value C16H25BNO2 ([MH]+) is 274.1973; measured value is 274.2256.