Potassium Carbonate → 2-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

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Reaction Steps

To a suspension of 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11, 300 mg, 0.88 mmol) and p-tolylboronic acid (313 mg, 2.3 mmol) in dimethoxyethane (6.3 mL) were added 2 M aqueous K2CO3 (2.2 mL, 4.4 mmol) and bis(triphenylphosphine)palladium(II) chloride (124 mg, 0.18 mmol), and the mixture were refluxed for 16 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give brown oil. It was partitioned between dichloromethane and water. The separated organic layer was dried (Na2SO4), evaporated, and purified by TLC with hexane/ethyl acetate (1:1) to afford 349 mg (quant.) of the title compound as white solids: MS (ESI) m/z 307 [M+H]+, 1H-NMR (CDCl3) δ 7.43-7.20 (8H, m), 3.87 (2H, t, J=6.4 Hz), 2.91 (2H, t, J=6.4 Hz), 2.40 (3H, s), 2.31 (3H, s), 2.28 (3H, s).

Provenance & Evidence