Sodium percarbonate → 7-(Bromomethyl)-4-(4-fluorophenyl)-2-quinolinecarboxamide

Participants

Reaction Steps

Sodium percarbonate (2.98 g, 9.50 mmol, 3.0 equiv.) in water (52.8 ml) was added dropwise to a solution of 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (2-1, 1.08 g, 3.17 mmol, 1.0 equiv.) in acetone (106 ml) and the reaction stirred for 1 hour at rt. The reaction was quenched with saturated KH2PO4 and the mixture was extracted with EtOAc (3×). The combined organic fractions were dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography (120 g SiO2, 0-100% EtOAc/hexanes) to afford 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carboxamide (3-1, 650 mg, 57%) as a white solid. LRMS m/z (M+H)+ 359.05 found, 359.19 required.

Provenance & Evidence