Potassium Carbonate → HCID 22933814, compound

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Reaction Steps

Under nitrogen, the 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (150 mg, 0.646 mmol) obtained in Example 734, (a) and 3-chloro-4-fluoronitrobenzene (125 mg, 0.710 mmol) were dissolved in N,N-dimethylformamide (2 ml), followed by adding thereto potassium carbonate (134 mg, 0.969 mmol), and the resulting mixture was stirred at 70° C. for 1.5 hours. After the reaction solution was cooled to room temperature, water was added thereto, followed by extraction with toluene/ethyl acetate=1/3. The 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 suspended in methanol (10 ml), followed by adding thereto a 4N-hydrochloric acid/1,4-dioxane solution (5 ml), and the resulting mixture was stirred at room temperature for 14 hours. (The residue was once dissolved and then gave a white suspension again). The resulting mixture was made basic by adding triethylamine slowly under ice-cooling, and the solvent was distilled off under reduced pressure. Then, water was added to the residue, followed by extraction with ethyl acetate. The extract layer was washed with 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, 2/1) to obtain 5-(2-chloro-4-nitrophenoxy)-4-methyl-1H-indazole (168 mg, yield 86%).

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