Sodium Carbonate → HCID 22177239, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-dimethylamino-2-(4-iodo-phenyl)-butyronitrile (1.02 g, 3.2 mmol) in 2:1 toluene/EtOH (30 mL) was added 2M Na2CO3 (10 mL, 20 mmol), pyridine-4-boronic acid pinacol cyclic ester (1.0 g, 4.9 mmol), and Pd(PPh3)4 (116 mg, 0.31 mmol). The resulting mixture was heated at 90° C. under Ar for 16 h. TLC (10% MeOH/CH2Cl2) showed no starting material left. The mixture was diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 (50 mL×3), saturated aqueous NaCl (50 mL×3), dried over Na2SO4 and concentrated by rotary evaporation. The crude residue was purified using silica gel chromatography (2–10% MeOH/CH2Cl2 gradient) to give 4-dimethylamino-2-(4-pyridin-4-yl-phenyl)-butyronitrile as a brown oil, 680 mg (80%). 1H NMR (300 MHz, CDCl3): δ 8.79 (dd, 2H), 7.78 (d, 2H), 7.60 (m, 4H), 4.22 (dd, 1H), 2.61 (m, 1H), 2.46 (m, 1H), 2.37 (s, 6H), 2.24 (m, 1H), 2.15 (m, 1H).

Provenance & Evidence