4-[5-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-cyclopentyl-6-methoxy-pyridine → 4-[5-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-2-ethyl-6-methyl-phenol

Participants

Reaction Steps

Pd/C (150 mg, 10% Pd) is added to a solution of 4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-cyclopentyl-6-methoxy-pyridine (750 mg, 1.60 mmol) in THF (20 mL) and methanol (20 mL). The mixture is stirred under 1 bar of H2 at rt for 24 h. The catalyst is removed by filtration and the filtrate is concentrated and dried to give 4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-2-ethyl-6-methyl-phenol (495 mg) as a white solid; LC-MS**: tR=0.91 min, [M+H]+=380.25; 1H NMR (D6-DMSO): δ 1.20 (t, J=7.5 Hz, 3H), 1.65-1.74 (m, 2H), 1.76-1.88 (m, 4H), 1.99-2.09 (m, 2H), 2.29 (s, 3H), 2.69 (q, J=7.5 Hz, 2H), 3.94 (s, 3H), 7.26 (d, J=1.0 Hz, 1H), 7.50 (d, J=0.8 Hz, 1H), 7.76 (d, J=2.0 Hz, 1H), 7.78 (d, J=2.0 Hz, 1H).

Provenance & Evidence