Sodium Thiosulfate → 7-[(4-Benzyloxy-pyridin-2-yl)-pyridin-2-yl-amino]heptanoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

NaH (245 mg, 6.38 mmol) was added to II (1.77 g, 6.38 mmol) in DMF (25 mL) at rt. After 15 min, KI (1.588 g, 9.57 mmol) and ethyl 7-bromoheptanoate (1.86 mL, 9.57 mmol) were added, and the reaction mixture was stirred at 90° C. for 17 h. Aqueous 0.1 M Na2S2O3 (100 mL) and EtOAc (100 mL) were added and the phases were separated. The organic phase was washed with brine (100 mL), dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 to 70:30) to furnish III as a yellow oil (1.321 g, 48%).

Provenance & Evidence