Binap, (A+-)- → N,N-dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

In a similar manner as described in Example 66, 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), 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide (21.9 mg, 0.102 mmol), (S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl ((S)-BINAP) (15.9 mg, 0.026 mmol), Tris(dibenzylidineacetone)dipalladium (0) (7.8 mg, 0.008 mmol) and sodium t-butoxide (11.4 mg, 0.12 mmol) in 1,4-dioxane (1.5 mL) were heated with microwave radiation at 140° C. for 60 minutes in a sealed reaction vessel to give N,N-dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}methanesulfonamide (0.0125 g) as a yellow solid. 1H NMR (CDCl3) δ8.80 (s, 1H), 8.15 (dd, J=1.8, 1.8 Hz, 1H), 8.06-8.04 (m, 1H), 7.36 (dd, J=8.0, 7.9 Hz, 1H), 7.25-7.22 (m, 2H), 7.16 (dd, J=1.9, 1.8, 1H), 7.10 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 6.93-6.91 (m, 4H), 6.10 (s, 1H), 4.17 (s, 2H), 3.84-3.83 (m, 9H) 2.76 (s, 6H), 2.60 (s, 3H). MS m/z 605 (M+1).

Provenance & Evidence