Silane, bromotriethyl- → 2-Bromo-1-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol

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To a mixture of 3-(4-(oxiran-2-yl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole (205 mg, 0.549 mmol) in THF (5 mL) at −78° C. was slowly added bromotriethylsilane (100 μL, 0.582 mmol). The reaction mixture was stirred for 1 hour at −78° C. LC/MS was employed to determine extent of reaction. An aliquot was removed and concentrated in vacuo. Crude NMR indicated mostly desired regioisomer. The reaction was quenched with water and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated. The solids were purified on a silica cartridge using an EtOAc/hexanes gradient to yield 130 mg of Preparation 1C as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.16-8.24 (2H, m), 7.72-7.81 (2H, m), 7.61 (2H, m, J=8.13 Hz), 7.49-7.58 (3H, m), 5.12 (1H, dd, J=7.47, 5.93 Hz), 4.09-4.17 (1H, m), 4.01-4.08 (1H, m), 2.97-3.05 (2H, m), 1.70-1.83 (2H, m), 1.06 (3H, t=7.36 Hz).

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