[CH:1]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2].[H-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17]I.[Na+].[Cl-]>CN(C=O)C.O>[Cl:14][CH2:15][CH2:16][CH2:17][O:11][C:7]1[CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:10]=[N:9][CH:8]=1
Under a nitrogen atmosphere, a solution of 5-isopropoxypyridin-3-ol (1.04 g, 6.80 mmol) in DMF (10 mL) was slowly added over 10 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.25 g of an 80% dispersion in mineral oil, 8.33 mmol) in DMF (15 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1 h. To this slurry was added drop-wise over 5 min, 1-chloro-3-iodopropane (1.67 g, 8.16 mmol), and the resulting dark brown mixture was stirred at ambient temperature for 4 h. Cold water (25 mL) was carefully added, followed by saturated NaCl solution (25 mL). The resulting mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation producing a dark-brown oil (0.92 g, 59.0%).
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