4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Methyl 4-(4'-amino-[1,1'-biphenyl]-4-yl)butanoate

Participants

Reaction Conditions

Reaction Steps

Solid 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (158 mg, 0.723 mmol) and Pd(PPh3)4 (38 mg, 0.033 mmol) were added to a solution of methyl 4-(4-iodophenyl)butanoate (200 mg, 0.657 mmol) in dimethoxyethane/2M Na2CO3 (3 mL, 2:1) at rt. The resulting mixture was degassed with argon gas then heated at 110° C. using microwave for 30 min. The reaction mixture was diluted with EtOAc (10 mL) then washed with H2O (10 mL), brine (10 mL), dried over Na2SO4, and concentrated to give crude (294 mg) as brown oil. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (146 mg, 82%) as a light yellow solid. ES/MS calcd. for C17H20NO2+ 270.2. Found m/z=270.2 (M+H)+.

Provenance & Evidence