Sodium Iodide → 2-{5-[2-(4-methoxy-phenyl)-ethyl]-7,8-dihydro-5H-[1,6]naphthyridin-6-yl}-N-methyl-2-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 615 mg (2.29 mmol) 5-[2-(4-methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine in 25 mL acetonitrile, were added 682 mg (2.98 mmol) 2-bromo-N-methyl -2-phenyl-acetamide, 1.2 mL (6.87 mmol) N-ethyldiisopropylamine and 343 mg (2.29 mmol) sodium iodide. The solution was stirred at 60° C. for 6 h. The solvent was removed in vacuo and the residue was taken in ethyl acetate. The mixture was washed once with water and once with a 2M Na2CO3 solution, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated to yield 330 mg (35%) of 2-{5-[2-(4-methoxy-phenyl)-ethyl]-7,8-dihydro-5H-[1,6]naphthyridin-6-yl}-N-methyl-2-phenyl-acetamide (diastereoisomer 1, first eluting diastereoisomer) as yellow foam

Provenance & Evidence