Sodium Chloride → HCID 22989721, compound

Under a nitrogen atmosphere, a solution of 5-bromo-3-hydroxypyridine (1.90 g, 10.92 mmol) in DMF (10 mL) was slowly added over 10 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.52 g of an 80% dispersion in mineral oil, 17.47 mmol) in DMF (14 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1H. To this slurry was added dropwise over 5 min 1-choro-3-iodopropane (2.68 g, 13.10 mmol), and the resulting dark-brown mixture was stirred at ambient temperature for 48 h. Cold water (30 mL) was carefully added, followed by saturated NaCl solution (20 mL). The resulting mixture was extracted with ether (5×25 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation producing a dark-brown oil (4.07 g). The product was used in the next step without further purification. EI-MS: m/z (relative intensity) 251 (M+, 31.89%), 249 (M+, 23.99%), 175 (65.68%), 173 (67.42%), 94 (37.06%), 41 (100.00%).

1. stirringthe resulting dark-brown mixture was stirred at ambient temperature for 48 h
2. extractionThe resulting mixture was extracted with ether (5×25 mL)
3. dry with materialThe combined ether extracts were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated by rotary evaporation

ORD record

ord-b108a80b7ba342c3b087cafba55c9b73

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166047