4-Bromotoluene → Methyl 1-(4-methylphenyl)-1H-indazole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1H-indazole-6-carboxylate (2.0 g, 11.4 mmol) in toluene (11.4 mL) was added 4-bromotoluene (2.33 g, 13.6 mmol), tribasic potassium phophate (4.8 g, 22.7 mmol), copper iodide (0.12 g, 0.60 mmol) and trans-(1R,2R)—N,N′-bismethyl-1,2-cyclohexanediamine (0.18 mL, 1.14 mmol). The reaction mixture was stirred in a sealed tube at 120° C. After 10 min, 4-iodotoluene (3.01 g) was added and the mixture was stirred at 120° C. for another 2 h. The mixture was cooled to ambient temperature and quenched with saturated sodium bicarbonate (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with saturated aqueous sodium chloride (1×15 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.76 g): LC-MS [M+1]=267.1.

Provenance & Evidence