Sodium hydride → HCID 58532561, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (119 mg, 2.97 mmol) was added to a stirred solution of tert-butyl 4-(2-hydroxypropyl)pyridin-2-ylcarbamate (47) (250 mg, 0.991 mmol) in DMF (6 mL) at 0° C., under nitrogen and after 45 min a solution of 1-fluoro-4-nitronaphthalene (14) (189 mg, 0.991 mmol) in DMF (6 mL) was added dropwise, over 2 min. The resulting dark-brown reaction mixture was stirred at 0° C. for 5 min, and was then warmed to RT. After 70 min, a saturated aqueous solution of NH4Cl (3 mL) was added and the mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g; 0-70% EtOAc in isohexane, gradient elution) to afford the title compound (48) (293 mg, 65%) as an orange foam: m/z 424.0 (M+H)+ (ES+).

Provenance & Evidence