Potassium Carbonate → 4-(3-methyl-5-nitrophenyl)-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (8.17 g, 27.8 mmol), tetrakis(triphenylphosphine)palladium(0) (2.67 g, 2.31 mmol) and potassium carbonate (12.8 g, 93.0 mmol) were added to a solution of 1-bromo-3-methyl-5-nitrobenzene (5.0 g, 23.1 mmol) in dioxane (7.5 mL). The mixture was degassed with nitrogen for 5 minutes and stirred at 100° C. for 18 h. The mixture was passed through CELITE, washed with methanol and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 4-(3-methyl-5-nitrophenyl)-1H-pyrazole. MS ESI calc'd. for C10H10N3O2 [M+H]+ 204. found 204.

Provenance & Evidence