Ethanol → HCID 136360287, compound

Participants

Reaction Steps

Palladium Acetate (0.365 g, 0.00162 mol) and Triphenylphosphine (0.442 g, 0.00168 mol) were dissolved in Tetrahydrofuran (20 mL, 0.3 mol) and the mixture was stirred at room temperature for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.943 g, 0.007959 mol) was added and the reaction was stirred for another 10 minutes. 2-hydroxyphenyl boronic acid (3.09 g, 0.022 mol) was added followed by saturated sodium carbonate solution (7.6 mL) and Ethanol (20 mL, 0.4 mol;). The reaction mixture was heated at 80° C. for 2 days. Brine was poured into the reaction mixture and organics were extracted three times into ethyl acetate. Combined organic layers were dried over sodium sulfate, filtered, concentrated and purified by normal phase silica gel chromatography eluting with ethyl acetate/heptane to yield a yellow solid, 2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (1.92 g, 94%). LCMS: m/z=258.02 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H), 8.97 (s, 1H), 7.87 (m, 1H), 7.22 (d, 1H, J=4.7 Hz), 7.12 (m, 1H), 7.05 (d, 1H, J=4.7 Hz), 7.01 (d, 1H, J=7.8 Hz), 6.93 (m, 1H), 2.47 (s, 3H).

Provenance & Evidence