A solution of 2-[4-(methylsulfonyl)phenyl]-5-({[1-(1H-tetrazol-5-yl)-4-piperidinyl]methyl}oxy)pyridine (157 mg, 0.38 mmol) in DMF (2 mL) and acetone (3 mL) was added potassium carbonate (105 mg, 0.76 mmol) at room temperature. After stirring for 15 min, 2-iodopropane (193 mg, 1.14 mmol) was added by syringe and the mixture was heated at 50° C. for 16 h. The salt was removed by filtration and washed with MeOH/CH2Cl2. After concentration, a small amount of MeOH/CH2Cl2 was added and the resulting precipitate was collected and washed with a small amount of MeOH. The material was dried in vacuo to give the title compound (130 mg, 71%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.34-8.25 (m, 2H), 8.07 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.7 Hz) 7.55 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 4.88 (septet, 1H, J=6.7 Hz), 4.03 (d, 2H, J=6.6 Hz), 3.98 (d, 2H, J=12.6 Hz), 3.25 (s, 3H), 3.01-2.86 (m, 2H), 2.11-1.95 (m, 1H), 1.94-1.82 (m, 2H), 1.50 (d, 6H, J=6.7 Hz), 1.46-1.30 (m, 2H); LRMS (ESI), m/z 457 (M+H).
