3-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole → 4-(5-{2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]propyl}-4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

n-BuLi (210 ml, 2.5 M in hex., 0.52 mmol) was added dropwise to a solution of 4-(4-cyclopropyl-5-methyl-4H-1,2,4-triazol-3-yl)pyridine (80 mg, 0.4 mmol) in THF (10 ml) at −78° C. under an atm. of nitrogen. After stirring for 15 min 3-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (115 mg, 0.4 mmol) in THF (2 ml) was added. The mixture was stirred for 2 h at −78° C. and then at r.t. for 1 h. The solvent was removed under reduced pressure and the desired product was obtained by prep. HPLC in 20 mg yield. 1H NMR: 0.7 (m, 2 H) 1.2 (ddd, 2 H) 1.6 (d, 3 H) 3.2 (dd, 1 H) 3.3 (ddd, 1 H) 3.6 (dd, 1 H) 3.9 (m, 1 H) 7.5 (t, 1 H) 7.6 (m, 1 H) 7.7 (m, 2 H) 8.0 (m, 1 H) 8.1 (t, 1 H) 8.7 (m, 2 H)

Provenance & Evidence