Iodoethane → HCID 178469308, compound

Participants

Reaction Steps

To a 0° C. solution of ethyl 3-ethyl-7-hydroxy-1H-indazole-5-carboxylate (prepared as described in Acid Preparation 2) (932 mg, 3.98 mmol) in DMF (28 mL) was added 60% NaH oil dispersion (159 mg, 3.98 mmol). This mixture was stirred at 0° C. for 1 hour before the dropwise addition of a solution of iodoethane (0.32 mL, 3.98 mmol) in DMF (3 mL). The mixture was kept at 0° C. for several hours before removal of the cooling bath and allowing the reaction to warm to room temperature while stirring overnight. The reaction was diluted with EtOAc, washed with saturated aqueous NaHCO3, saturated aqueous NaCl, the organic extract was then dried over Na2SO4, filtered and concentrated. Purify by CombiFlash (80 g column, 0-30% EtOAc/hexanes) to provide ethyl 7-ethoxy-3-ethyl-1H-indazole-5-carboxylate (389 mg, 37%) and ethyl 7-ethoxy-1,3-diethyl-1H-indazole-5-carboxylate (202 mg).

Provenance & Evidence