Diisopropylamine → [5-(Benzyloxy)pyridin-2-yl](3-fluoropyridin-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (2.08 g) in THF (50 mL) was added 1.6 M n-BuLi in hexane (12.3 mL) at −5° C. The mixture was stirred for 15 min. The mixture was cooled to −78° C., and a solution of 3-fluoropyridine (1.74 g) in THF (10 mL) was added. The mixture was stirred for 1 h. To the mixture was added a solution of 5-(benzyloxy)-N-methoxy-N-methylpicolinamide (4.87 g) in THF (5 mL). The mixture was stirred at −78° C. for 2 h. The mixture was quenched with saturated NH4Cl aqueous solution at −78° C. and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.87 g).

Provenance & Evidence