Acrylamide → HCID 58711931, compound

Participants

Reaction Steps

To a mixture of 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (0.054 g, 0.12 mmol), acrylamide (0.025 g, 0.35 mmol), palladium (II) acetate (2.7 mg, 0.012 mmol) and tris(o-tolyl)phosphine (7.3 mg, 0.024 mmol) in acetonitrile (1 mL) was added triethylamine (0.050 mL, 0.35 mmol). The solution was heated to reflux for 30 minutes. After cooling to room temperature, the solution was filtered, and silica gel (1 g) was added, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexanes (50:50) to ethyl acetate:hexanes (100:0) to ethyl acetate:methanol (99:1) using a RediSep silica gel cartridge (4 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give (2E)-3-(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]-imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)prop-2-enamide (0.0046 g) as a yellow solid. 1H NMR (CD3OD): δ9.05 (s, 1H), 8.49 (s, 1H), 8.37 (d, J=7.3 Hz, 1H), 7.67-7.51 (m, 4H), 7.05 (s, 2H), 6.68 (d, J=15.9 Hz, 1H) 3.74 (s, 3H), 3.72 (s, 6H), 2.60 (s, 3H). MS m/z 461 (M+1).

Provenance & Evidence