Triphenylphosphine → 2-Bromo-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine

Participants

Reaction Steps

2-Bromo-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine (1 g, 60%) was prepared from {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 1 g, 4.4 mmol), 6-bromo-3-pyridinol (522 mg, 3 mmol), Ph3P (1.15 g, 4.4 mmol), diisopropyl azodicarboxylate (0.866 mL, 4.4 mmol), diisopropyl azodicarboxylate (0.866 mL, 4.4 mmol), and THF (15 mL) in a manner similar to Example 1, Step 2, and purified by reverse-phase preparative HPLC using a CH3CN:H2O gradient (30:70 to 100:0) with 0.05% TFA as a modifier. 1H NMR (400 MHz, CDCl3): δ 8.04 (d, 1H, J=3.1 Hz), 7.37 (d, 1H, J=8.7 Hz), 7.08 (dd, 1H, Ja=8.7 Hz, Jb=3.2 Hz), 4.22 (d, 2H, J=13.1 Hz), 3.85 (d, 2H, J=6.3 Hz), 3.09 (m, 2H), 2.89 (m, 1H), 2.13-1.99 (m, 1 H), 1.93 (d, 2H, J=12.4 Hz), 1.54-1.35 (m, 2H), 1.28 (d, 6H, J=6.9 Hz); LRMS (ESI m/z 381/383 (M+H).

Provenance & Evidence