4-(1H-imidazol-1-yl)aniline → 7-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine

Participants

Reaction Steps

In a similar manner as described in Example 63, 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) (40 mg, 0.085 mmol), 4-(1H-imidazol-1-yl)aniline (13.5 mg, 0.085 mmol), 2-(dit-butylphosphino)biphenyl (15.2 mg, 0.051 mmol), Tris(dibenzylidineacetone)-dipalladium (0) (15.6 mg, 0.017 mmol) and sodium t-butoxide (13.1 mg, 0.136 mmol) in 1,4-dioxane (1.5 mL) gave 7-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine (0.0126 g) as a yellow solid. 1H NMR (CDCl3): δ8.80 (s, 1H), 8.24 (s, 1H), 8.05 (d, J=7.3 Hz, 1H), 7.78 (s, 1H), 7.40-7.35 (m, 1H), 7.26-7.19 (m, 7H), 6.97-6.93 (s, 3H), 6.21 (s, 1H), 3.82 (s, 9H), 2.60 (s, 3H) MS m/z 549 (M+1).

Provenance & Evidence