Potassium Phosphate, Tribasic → 4-Amino-3-cyclopropylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (798 mg, 3.55 mmol) was added to a stirred mixture of 4-amino-3-iodobenzonitrile (5.08 g, 20.8 mmol), cyclopropyl boronic acid (2.69 g, 31.3 mmol), potassium phosphate (22.9 g, 108 mmol) and tricyclohexylphosphine (1.17 g, 4.17 mmol) in toluene (40 mL)/water (2 mL). The reaction mixture was degassed and heated to 100° C. for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution; 0-20% EtOAc/hexanes as eluent) to afford the title compound i-4-a. m/z (ES) 159 (MH)+

Provenance & Evidence