Sodium t-butoxide → 1-[2-Fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-4-{[1-(1-methylethyl)-4-piperidinyl]methyl}piperidine

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Sodium tert-butoxide (0.084 g) was added to a solution 1-(1-methylethyl)-4-(4-piperidinylmethyl)piperidine (may be prepared as described in Description 4) (0.156 g), 5-(4-bromo-3-fluorophenyl)-3-methyl-1,2,4-oxadiazole (may be prepared as described in Description 15) (0.150 g) and acetato(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium(II) (0.023 g) in toluene (10 ml). The reaction mixture was heated under argon at 80° C. overnight. After cooling to room temperature, the reaction mixture was passed through an SCX column (10 g, eluting with methanol [80 ml] then 2N NH3 in methanol [80 ml]) to afford the title compound (E14) (0.065 g). MS electrospray (+ion) 401 (MH+). 1H NMR δ (CDC13): 7.79 (1H, dd, J=2, 8 Hz), 7.73 (1H, dd, J=2, 13.6 Hz), 7.00 (1H, t, J=8.6 Hz), 3.62 (2H, m), 2.90 (2H, m), 2.84-2.69 (3H, m), 2.44 (3H, s), 2.12 (2H, m), 1.77 (2H, m), 1.69 (2H, m), 1.56 (1H, m), 1.42-1.22 (7H, m), 1.05 (6H, d)

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