Dimethylformamide → 1-(4-methoxybenzyl)-3-methyl-5-nitro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

3-methyl-5-nitro-1H-indazole (1.0 g, 5.6 mmol) was dissolved in DMF (11.2 mmol) and cesium carbonate (2.0 g, 6.2 mmol) added. The slurry was cooled to 0° C. and p-methoxy benzyl chloride (0.97 g, 6.2 mmol) added to vigorously stirred slurry drop wise. The slurry was stirred at 0° C. for 1 hour, the cooling bath removed and the mixture stirred at RT for 3 h. The mixture was diluted with 4:1 water:saturated sodium bicarbonate (200 ml), extracted with EtOAc (3×50 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 30% acetone:hexanes to give the titled compound.

Provenance & Evidence