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

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1,7-dihydro-1-phenylpyrazolo[3,4-b]pyridin-6-one (0.29 g, 1.0 mmol) in DMF (4 ml) under nitrogen was added cesium carbonate (0.98 g, 3.0 mmol) followed by 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (0.25 g, 1.5 mmol). The resulting suspension was heated at 60° C. for 17 h. The mixture was partitioned between ammonium chloride solution (saturated aqueous) and ethyl acetate. The layers were separated and the aqueous phase extracted a second time with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give 5-bromo-6-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1H-pyrazolo[3,4-b]pyridine (0.40 g) of adequate purity. δH (400 MHz; CDCl3) 4.04 (3H, s), 5.70 (2H, s), 7.33-7.37 (1H, m), 7.52-7.56 (2H, m), 7.90 (1H, s), 8.06 (1H, s), 8.16-8.19 (2H, m), 8.27 (1H, s); m/z (ES+) 387 (M+H+), 385 (M+H+).

Provenance & Evidence