Iodoethane → HCID 66920431, compound

Participants

Reaction Steps

To a solution of ethyl 7-hydroxy-1H-indazole-5-carboxylate (918 mg, 4.45 mmol) in DMF (35 mL) at 0° C. was added 60% oil dispersion of NaH (178 mg, 4.45 mmol). The mixture was aged for 1 hour at 0° C. before dropwise addition of a solution of iodoethane (694 mg, 0.36 mL, 4.45 mmol) in DMF (15 mL). The mixture was aged at 0° C. for several hours before removal of the ice bath. The reaction was allowed to warm to room temperature and aged overnight. The mixture was diluted with EtOAc, washed with water, saturated aqueous NaCl, dried over Na2SO4, filtered concentrated. Purify by silica gel chromatography (40 g column) eluting with 0-30% EtOAc/hexanes gradient to afford ethyl 7-ethoxy-1H-indazole-5-carboxylate (400 mg, 38%).

Provenance & Evidence