Tetrahydro-4H-pyran-4-one → 4-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-YL)tetrahydro-2H-pyran-4-OL

Participants

Reaction Steps

To a suspension of N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amine (1 g, 2.92 mmol) in THF (10 mL) at room temperature was added isopropylmagnesium chloride (5.11 mL, 10.23 mmol). After 1 h stirring at room temperature, another equal amount of isopropylmagnesium chloride was added and the resulting mixture was stirred at room temperature overnight. To the solution was added dropwise dihydro-2H-pyran-4(3H)-one (0.540 mL, 5.84 mmol) and stirring was continued for 1 h. Reaction was quenched with saturated NH4Cl and extracted with DCM. Purification by Biotage produced the product. MS (ESI, pos. ion) m/z: 364.0. IC50 (uM) 0.04172.

Provenance & Evidence