Methyl iodide → Tert-butyl(1-(4-(6-methyl-5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(5-oxo-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (30 mg, 0.06 mmol) in dry DMF (1 mL) was added sodium hydride (3 mg, 0.07 mmol) at 0° C. under nitrogen. After 1 h at 0° C., iodomethane (17 μL, 0.19 mmol) was added and the resulting mixture was stirred for an additional 10 min at 0° C. A saturated solution of NH4Cl was added and the mixture was extracted with dichloromethane (3×) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel chromatography (gradient 0 to 50% EtOAc in hexane) to give the title compound (22 mg, 71%). 1H NMR (500 MHz, CDCl3): 8.35 (1H, s), 7.34 (2H, d), 7.29 (2H,d), 7.24-7.22 (3H, m), 7.19-7.17 (2H, m), 5.06 (1H, br s), 3.70 (2H, t), 3.29 (2H, t), 3.19 (3H, s), 2.54-2.30 (4H, m), 2.08-2.00 (1H, m), 1.83-1.74 (1H, m), 1.44-1.18 (9H, br).

Provenance & Evidence