Tetrabutylammonium Fluoride → 4-[(5-Methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)-methyl]phenol

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Reaction Steps

To a solution of 5-[5-methyl-1-(4-{[tris(1-methylethyl)silyl]oxy}benzyl)-1H-pyrazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole (Step 1, 500 mg, 0.873 mmol) in THF (20 mL) was added a solution of tetrabutylammonium fluoride (1M in THF, 960 μl, 0.96 mmol) at a temperature of 0° C. The cooling bath was removed, and the reaction mixture was stirred at rt for 1 h. After the addition of water (100 μL), most of the organic solvent was removed in vacuo and replaced by methanol (1 mL). The crude mixture was subjected to preparative HPLC to afford the title compound in pure form (416 mg, 67%): 1H NMR (400 MHz, CDCl3) 8.24 (d, 2H), 7.32 (d, 2H), 7.07 (d, 2H), 6.79 (d, 2H), 6.78 (s, 1H), 5.61 (broad, 1H), 5.35 (s, 2H), 2.28 (s, 3H); ES-MS m/z 417, HPLC RT (Method J) 4.78 min.

Provenance & Evidence