Dimethylformamide → HCID 66920633, 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) (50 mg, 0.21 mmol) in DMF (1 mL) was added 60% NaH oil dispersion (8.5 mg, 0.21 mmol). This mixture was stirred for 30 minutes before addition of iodomethane (0.011 mL, 0.17 mmol). The reaction was kept at 0° C. for 2 hours before allowing to alowly warm to room temperature while stirring overnight. The reaction was diluted with EtOAc and saturated aqueous NaHCO3. The organic phase was isolated and the aqueous phase was back extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated. The crude product was purified by CombiFlash (12 g column, 0-30% EtOAc/hexanes) to provide 3-ethyl-7-methoxy-1H-indazole-5-carboxylate (22 mg, 41%) and ethyl 3-ethyl-7-methoxy-1-methyl-1H-indazole-5-carboxylate (46 mg, 60%).

Provenance & Evidence