I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2ON=C(C(=O)C)[N:21]=2)=[CH:16][CH:15]=1.C1C[O:31]CC1>>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:9]=[C:10]([CH:11]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH3:12])[O:31][N:21]=2)=[CH:18][CH:19]=1To a stirred solution of 4-iodopyridine (0.29 g, 0.463 mmol) in THF (30 mL) at −78° C. was added n-BuLi (2.4 mL, 3.9 mmol) and the mixture was stirred for 10 min 1-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)ethanone (0.5 g, 2.79 mmol) in THF (5 mL) was then added to reaction, which was then stirred at −78° C. for 2 h. The reaction was then quenched with saturated ammonium chloride solution (10 mL) and diluted with ethyl acetate (50 mL). The organic layer was separated, washed with ammonium chloride solution (3×150 mL) followed by brine solution (2×20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain crude product. The crude product was purified by column chromatography (100-200μ silica gel and 30% ethyl acetate in hexane) to obtain 3-(4-fluorophenyl)-5-(1-(pyridin-4-yl)ethyl)isoxazole as off-white solid (0.06 g, 29% yield). 1H NMR (400 MHz, CDCl3): δ 8.60 (d, 2H), 8.11 (dd, 2H), 7.48 (d, 2H), 7.19 (t, 2H), 3.40 (s, 1H), 1.99 (s, 3H); LC-MS m/z calculated for [M+H]+286.09. found 286.2.
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