Cesium carbonate → racemic 4-(5-{1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine

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Reaction Steps

0.57 g (2.54 mmol) (+)-(1R)-1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethanol, 0.64 g (2.68 mmol) 4-[4-methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyridine and 0.90 g (2.76 mmol) cesium carbonate were stirred at 65° C. for 6 h, followed by dilution with water. Extraction with EA, washing with aq. citric acid, drying over Na2SO4, followed by purification via chromatotron 2 mm (Hep/EA/MeOH=10/10/1) gave 0.81 g (83%) racemic 4-(5-{1-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine. Prep. chiral separation on Chiralpak AD using 100% 2-propanol yielded 0.25 g of the title compound as the second eluting enantiomer. 1H NMR: 8.76 (d, 2 H), 8.07 (t, 1 H), 7.92-7.99 (m, 1 H), 7.60-7.68 (m, 2 H), 7.45-7.51 (m, 1 H), 7.41 (t, 1 H), 6.45 (q, 1 H), 3.66 (s, 3 H), 1.99 (d, 3 H)

Provenance & Evidence