Ethanol → N-(2,4-dimethoxybenzyl)-1-(2',5-dimethyl-3,4'-bipyridin-6-yl)methanamine

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 1-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine 81-3 (1.5 g, 4.3 mmol), 2-methylpyridin-4-ylboronic acid 15-1 (589 mg, 4.3 mmol), Pd(PPh3)4 (248 mg, 0.22 mmol), saturated Na2CO3 (10 mL), ethanol (10 mL) and toluene (30 mL). The reaction was refluxed at 120° C. for 30 hours. After cooling to room temperature, the reaction was diluted into ethyl acetate and washed with brine. The solvent was removed by rotary evaporation. The crude product was purified by silica gel flash chromatography to give N-(2,4-dimethoxybenzyl)-1-(2′,5-dimethyl-3,4′-bipyridin-6-yl)methanamine 81-4. MS m/z 364.2 (M+1).

Provenance & Evidence