Sodium hydride → 5-bromo-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3,5-dibromopyridine (1.5 g, 6.05 mmol) and 60% NaH (307 mg, 7.7 mmol) in DMF (6 mL) was added 1-tosyl-2-(S)-pyrrolidinemethanol (1.4 g, 5.5 mmol), and the reaction mixture was stirred for 4 hours at room temperature and 1 hour at 60° C. The DMF was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane 6:1 to afford the title compound (1.2 g).

Provenance & Evidence