Sodium Iodide → HCID 59375501, compound

Participants

Reaction Conditions

Reaction Steps

9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (120 mg, 0.31 mmol), copper(I) iodide (5.9 mg, 0.031 mmol), and sodium iodide (93 mg, 0.62 mmol) were combined in a vial. Butan-1-ol (1.0 ml) and trans-(1R,2R)—N,N-bismethyl-1,2-cyclohexanediamine (9.9 μl, 0.062 mmol) were added, and the resulting suspension was purged with argon (subsurface bubbling) for 5 min. The reaction mixture was heated to 130° C., and stirred for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (40 mL) and brine (40 mL). The organic layer was washed with additional brine (1×40 ml). The first aqueous layer was back-extracted with ethyl acetate (1×40 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (solid SiO2 loading) using an EtOAc/Hexanes gradient to afford 9-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C18H20IN3O) [M+H]+, 422.1; found 422.0.

Provenance & Evidence