2-(Di-tert-butylphosphino)biphenyl → N-methyl-N-[4-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]urea

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-(4-bromophenyl)-N-methylurea (0.02 g, 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 N-methyl-N-[4-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]urea (0.016 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.11 (s, 1H), 8.99-8.95 (m, 1H), 8.82-8.76 (m, 1H), 8.69-8.66 (m, 1H), 7.95-7.91 (m, 1H), 7.80-7.76 (m, 2H), 7.74-7.69 (m, 3H), 7.57-7.52 (m, 2H), 6.30 (bs, 1H), 5.61 (bs, 1H), 2.76 (d, J=4.8 Hz, 3H), 2.57 (s, 3H). MS m/z 442 (M+1).

Provenance & Evidence