N-(2-(p-bromophenoxy)ethyl)pyrrolidine → 5-methyl-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine

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), 1-[2-(4-bromophenoxy)ethyl]pyrrolidine (0.016 mL, 0.09 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 5-methyl-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (0.031 g) as a yellow solid. 1H NMR (CD3OD): δ9.04 (s, 1H), 8.84 (s, 1H), 8.53 (d, J=7.3 Hz, 1H), 8.34 (bs, 2H), 7.75-7.64 (m, 4H), 7.02 (d, J=8.8 Hz, 2H), 4.33 (t, J=4.8 Hz, 2H), 3.66 (t, J=4.8 Hz, 2H), 3.48 (bs, 4H), 2.58 (s, 3H), 2.13 (bs, 4H). MS m/z 483 (M+1).

Provenance & Evidence