Sodium hydride → 8-chloro-2-methyl-5H-chromeno[3,4-c]pyridine

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Reaction Steps

To a stirred solution of (4-(4-chloro-2-fluorophenyl)-6-methylpyridin-3-yl)methanol (0.25 g, 0.993 mmol) in tetrahydrofuran (25 mL) at 0° C. was added NaH (0.06 g, 1.49 mmol) portionwise. The solution was then stirred for 16 h at RT. The reaction mixture was quenched with water (100 mL). The precipitate was collected by filtration and air dried to afford 8-chloro-2-methyl-5H-chromeno[3,4-c]pyridine (0.2 g, 0.863 mmol, 69% yield) as a white solid. LCMS (ESI) m/e 232.0 [(M+H)+, calcd for C13H11ClNO 232.0]; LC/MS retention time (Method D): tR=2.06 min; 1H NMR (400 MHz, CDCl3) δ 8.31 (s, 1H), 7.65 (d, J=4.40 Hz, 1H), 7.37 (s, 1H), 7.07-7.03 (m, 2H), 5.14 (s, 2H), 2.61 (s, 3H).

Provenance & Evidence