DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE

124-40-3

214360-74-4

909391-56-6

Step X1 Intermediate XI.1: 2-(3-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (297 mg, 1.0 mmol) was dissolved in acetonitrile (5 mL), a methanol solution of dimethylamine (2 M, 1.0 mL, 2.0 mmol) was added followed by potassium carbonate (691 mg, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, acetonitrile was removed under vacuum and the residue was partitioned with ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered and the filtrate was concentrated to afford dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine (Intermediate XI.1) as a viscous oily substance (200 mg, 0.77 mmol, 77% yield). Characterization data for intermediate XI.1: 1H NMR (300 MHz, CD3OD): δ 7.70 (m, 2H), 7.30-7.45 (m, 2H), 3.50 (s, 2H), 2.28 (s, 6H), 1.36 (s, 12H) ppm; MS (ESI), m/z: 262 ([M + H]+).