N-(3-bromo-4-methoxyphenyl)acetamide → N-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide

Participants

Reaction Steps

In a similar manner as described for Example 41, 5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (intermediate 45) (0.025 g, 0.09 mmol), N-(3-bromo-4-methoxyphenyl)acetamide (0.044 g, 0.18 mmol), Pd2(dba)3 (0.008 g, 0.01 mmol), 2-(Di-t-butylphosphino)biphenyl (0.008 g, 0.03 mmol), and NaOtBu (0.011 g, 0.11 mmol) in 1,4-dioxane (1 mL) gave N-[4-methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide (0.007 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.15 (s, 1H), 9.06 (bs, 1H), 8.98 (d, J=7.6 Hz, 1H), 8.73 (s, 1H), 8.53 (d, J=2.4 Hz, 1H), 7.83-7.70 (m, 3H), 7.30 (dd, J=8.7, 2.3 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 3.94 (s, 3H), 2.59 (s, 3H), 2.09 (s, 3H). MS m/z 457 (M+1).

Provenance & Evidence