Sodium hydride → 4-(1-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-2-amine

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Reaction Conditions

Reaction Steps

To a stirred solution of 1-(2-aminopyridin-4-yl)ethanol (37) (73 mg, 0.528 mmol) in DMF (1.5 mL), under nitrogen at 0° C., was added sodium hydride (32 mg, 0.793 mmol, 60 wt %). The resulting mixture was stirred at 0° C. for 40 min, and a solution of 1-fluoro-4-nitronaphthalene (14) (101 mg, 0.528 mmol) in DMF (1.5 mL) was added dropwise. The resulting dark-red mixture was stirred at 0° C. for 5 min and at RT for 40 min and was quenched by the addition of 1.0 mL of NH4Cl solution. Water (20 mL) and EtOAc (20 mL) were added, and the layers were separated. The aqueous layer was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried and the solvents removed in vacuo. The crude material was purified by column chromatography (SiO2, 12 g, 0-80% EtOAc in isohexane, gradient elution) to give the title compound (38) (94.6 mg, 57%) as an orange gum: m/z 310 (M+H)+ (ES+).

Provenance & Evidence