Potassium Carbonate → methyl 1-((4-methoxyphenyl)methyl)-1H-indazole-3-carboxylate

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Methyl 3-indazolylcarboxylate (2.0 g, 11.4 mmol) was dissolved in DMF (20 ml). To the resulting solution were added 4-methoxybenzyl chloride (1.7 ml, 12.5 mmol) and potassium carbonate (2.35 g, 17.0 mmol). The resulting mixture was stirred at 80° C. for 15 hours. After cooling, the reaction mixture was poured in water (50 ml), followed by extraction with ethyl acetate (200 ml). The extract was washed with saturated brine (2×100 ml), dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, methyl 1-(4-methoxybenzyl)-3-indazolylcarboxylate (polar fractions, 838 mg, 25%) was obtained as a pale yellow oil and 2(4-methoxybenzyl) isomer (non-polar fractions, 500 mg, 15%) was obtained as a pale yellow oil.

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