Sodium Carbonate → HCID 66682602, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium complex (0.076 g, 0.066 mmol) was added to a stirred dispersion of N-(1-benzylpiperidin-4-yl)-4-(3-bromophenyl)-N-methyl-1H-imidazole-1-carboxamide (0.600 g, 1.323 mmol), 3-carbamoylphenylboronic acid (0.229 g, 1.390 mmol) and a 2 M solution of sodium carbonate (0.794 mL, 1.588 mmol) in a mixture of 1-propanol (5 mL) and water (1 mL) at room temperature. The reaction mixture was allowed to stir at 90° C. for 1 h. Water was added and the organic layer was diluted with a mixture of dichloromethane/isopropanol (7:3). The organic layer was separated, dried (MgSO4), filtered and evaporated to give an orange oil. Column chromatography (silica, dichloromethane/methanol 5%) gave the product as an orange oil. The oil was triturated with a mixture of petroleum ether/ethyl acetate/ether to give the product as a beige solid (123 mg, 17%).

Provenance & Evidence