Isopropanol → 8-Isopropoxy-2-methyl-[1,5]naphthyridine

Participants

Reaction Conditions

Reaction Steps

To a 100 mL flask placed with KH (30%, 2.7 g, 20.15 mmol, pre-washed with nHex) was added a solution of anhydrous isopropanol (2.04 g, 33.59 mmol) in anhydrous THF (15 mL) at room temperature under argon. The reaction mixture was cooled to −20° C. 8-chloro-2-methyl-[1,5]naphthyridine (1.20 g, 6.72 mmol) in THF (20 mL) was added dropwise and the reaction mixture was stirred at −20° C. to r.t for 2 hrs. The reaction mixture was poured into 20 mL ice-water and extracted with AcOEt (100 mL×3). The combined organic layers was dried over Na2SO4 and concentrated to give the crude product which was purified by flash column (AcOEt/Hex=1/3˜3/2) to give 8-isopropoxy-2-methyl-[1,5]naphthyridine as white solid (0.34 g, 25%). HR-MS-EI (+) m/e calcd for C12H14N2O (M+) 202.1106. found 202.1107.

Provenance & Evidence