Sodium bis(trimethylsilyl)amide → 3-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-phenylamino-pyridin-3-yl)-propan-1-one (2.0 g, 8.84 mmol) in THF (17.7 mL) at 25° C. was treated with sodium bis(trimethylsilyl)amide (1.0 M in THF) (22.1 mL, 22.1 mmol). The resulting red solution was then treated with a mixture of oxazole-2-carbonyl chloride (1.51 g, 11.5 mmol) in THF (8 mL) and 10 drops of DMF. The reaction was then stirred at 25° C. overnight. The reaction was diluted with water (50 mL) and was then extracted into ethyl acetate (3×50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was absorbed onto silica and dried under high vacuum. Flash chromatography (25 g, 25%-75% ethyl acetate-hexanes) afforded 3-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (540 mg, 20.1%) as a light yellow solid.

Provenance & Evidence