2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → 4-{[tert-butyl(dimethyl)silyl]oxy}-1-[3-(1H-1,2,3-triazol-1-yl)phenyl]piperidine

関与物質

反応条件

反応手順

A dioxane (5 mL) solution of 1-(3-bromophenyl)-1H-1,2,3-triazole (224 mg, 1.00 mmol) and 4-{[tert-butyl(dimethyl)silyl]oxy}piperidine (323 mg, 1.50 mmol) was degassed with bubbling nitrogen in a vial. 2-(Dicyclohexylphosphino)-2′-(dimethylamino)biphenyl (20 mg, 0.051 mmol), palladium(II)acetate (11 mg, 0.050 mmol), and sodium tert-butoxide (384 mg, 4.0 mmol) were then added. The reaction mixture was degassed again, and the vial was sealed. It was heated to 100° C. for 20 hours and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 7.96 (s, 1H), 7.83 (s, 1H), 7.38-7.31 (m, 2H), 7.02 (d, J=7.9 Hz, 1H), 6.98 (d, J=8.5 Hz, 1H), 3.97-3.89 (m, 1H), 3.53 (ddd, J=12.4, 7.5, 3.5 Hz, 2H), 3.16 (ddd, J=12.5, 7.8, 3.5 Hz, 2H), 1.95-1.81 (m, 2H), 1.72-1.64 (m, 2H), 0.90 (s, 9H), 0.08 (s, 6H); LC-MS: m/z 359.1 (M+H).

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