Ethyl Acetate → HCID 18404021, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-bromo-1,2,3-triazolo[4,5-b]pyridine (0.10 g, 0.247 mmol) (Example 3, step c), 3-thiopheneboronic acid (0.080 g, 0.60 mmol), caesium carbonate (0.26 g, 0.80 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.03 g, 10 mol %) in DMF (4 ml) and water (1 ml) was purged with nitrogen, then heated in a sealed tube at 100° C. for 5 h. The solution was cooled, diluted with water (50 ml) and extracted with 10% methanol-dichloromethane (2×30 ml). The extracts were washed with brine (30 ml), dried (Na2SO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 4% methanol-dichloromethane, gave a brown gum that solidified on trituration with ethyl acetate. The material was recrystallised from ethyl acetate to give 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-(thien-3-yl)-1,2,3-triazolo[4,5-b]pyridine (0.059 g, 59%) as a beige solid, m.p. 133-135° C. (EtOAc). Found: C, 55.31; H, 3.38. C19H14N7OFS requires C, 55.40; H, 3.55%. δH (360 MHz; CDCl3) 3.73 (3H, s), 5.60 (2H, s), 7.36-7.46 (4H, m), 7.56-7.62 (1H, m), 7.66 (1H, dd, J=3 and 1), 7.71 (1H, dd, J=8 and 8), 7.86 (1H, s) and 8.46 (1H, s); m/z (ES+) 408 (M+H+).

Provenance & Evidence