Hydrochloric Acid → HCID 22933895, compound

Participants

Reaction Steps

Under nitrogen, 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (200 mg, 0.861 mmol) was dissolved in N,N-dimethylformamide (5 ml), followed by adding thereto 4-fluoronitrobenzene (100 μl, 0.947 mmol) and potassium carbonate (179 mg, 1.29 mmol), and the resulting mixture was stirred at 50° C. for 1 hour. After the reaction solution was cooled to room temperature, a 1N-aqueous hydrochloric acid solution (6 ml) and methanol (3 ml) were added thereto and the resulting mixture was stirred at room temperature for 2 hours. The mixture was adjusted to pH 9 with a saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate/toluene=3/1. The combined extract layer was washed with water and then a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain 4-methyl-5-(4-nitrophenoxy)-1H-indazole (192 mg, yield 82.8%) as a yellow solid.

Provenance & Evidence