Cesium carbonate → 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine

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Reaction Steps

A mixture of 3-phenyl-6-(tert-butyl)-3,4-dihydro-1,2,3-triazolo[4,5-b]pyridin-5-one (0.025 g, 0.093 g), 2-methyl-3-chloromethyl-1,2,4-triazole hydrochloride (0.15 g, 1.1 mmol) and cesium carbonate (0.65 g, 2.0 mmol) in dry DMF (4 ml) was stirred at r.t. for 20 h. The mixture was diluted with water (50 ml) and 1M citric acid (5 ml), and extracted with dichloromethane (2×25 ml). The extracts were dried (Na2SO4), filtered and concentrated. Preparative thin-layer chromatography, eluting with 5% methanol-dichloromethane, gave 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine (0.028 g, 83%) as a white solid, m.p. 165-167° C. δH (360 MHz; CDCl3) 1.43 (9H, s), 3.94 (3H, s), 5.69 (2H, s), 7.46 (1H, t, J=7), 7.60 (2H, dd, J=7 and 7), 7.93 (1H, s), 8.20 (2H, d, J=7) and 8.31 (1H, s); m/z (ES+) 364 (M+H+).

Provenance & Evidence