Methyl iodide → HCID 178469302, compound

Participants

Reaction Steps

To a solution of ethyl 7-hydroxy-3-methyl-1H-indazole-5-carboxylate (Anti-Cancer Drug Design 1997, 12, 555) in DMF (25 mL) at 0° C. was added 60% oil dispersion of NaH (152 mg, 3.81 mmol). The mixture was stirred for 1 hour before the dropwise addition of a solution of iodomethane (0.54 g, 0.24 mL, 3.8 mmol) in DMF (3 mL). The mixture was kept at 0° C. for several hours before allowing the mixture to warm to room temperature and stirred overnight. The reaction was diluted with EtOAc, saturated aqueous NaHCO3, water and saturated aqueous NaCl. The organic extract was dried over Na2SO4, filtered and concentrated. The material was purified by silica gel chromatography (80 g column) eluting with a 0-30% EtOAc/hexanes gradient to provide ethyl 7-methoxy-3-methyl-1H-indazole-5-carboxylate (294 mg, 33%).

Provenance & Evidence