反应详情

To a solution of (3-amino-pyridin-4-yl)-methanol (13) (4.00 g, 32.2 mmol) in anhydrous THF (160 mL) at 0° C. was added sodium hydride (1.55 g, 38.7 mmol, 60 wt %). After stirring for 20 min, 1-fluoro-4-nitronaphthalene (14) (6.16 g, 32.2 mmol) was added, the ice bath was removed and the reaction mixture left to warm to RT and stirred for 12 hr. The reaction mixture was partitioned between EtOAc (200 mL) and saturated aq NaHCO3 solution (150 mL). The remaining yellow solid was collected by filtration and washed sequentially with water (50 mL), MeOH (50 mL) and diethyl ether (100 mL) and was identified as the desired product by LC-MS and 1H NMR. The filtrate was returned to a separating funnel; the organic phase was collected and washed with brine (100 mL), dried and concentrated in vacuo to afford an orange residue. Trituration of the orange residue with MeOH (200 mL) afforded an orange solid which was washed with diethyl ether (200 mL). LC-MS and 1H NMR analysis of the orange solid was identical to that observed for the insoluble solid obtained earlier. The two products were combined to afford the title compound (15) (7.80 g, 77%): m/z 296 (M+H)+ (ES+).

1. customthe ice bath was removed
2. waitthe reaction mixture left
3. stirringstirred for 12 hr
4. customThe reaction mixture was partitioned between EtOAc (200 mL) and saturated aq NaHCO3 solution (150 mL)
5. filtrationThe remaining yellow solid was collected by filtration
6. washwashed sequentially with water (50 mL), MeOH (50 mL) and diethyl ether (100 mL)
7. customThe filtrate was returned to a separating funnel
8. customthe organic phase was collected
9. washwashed with brine (100 mL)
10. customdried
11. concentrationconcentrated in vacuo
12. customto afford an orange residue
13. washwas washed with diethyl ether (200 mL)
14. customobtained earlier