3-Methyl-4-phenoxyaniline → 2-Chloro-N-{3-[4-(3-methyl4-phenoxy-phenylamino)-quinazolin-6-yl]-prop-2-ynyl}-acetamide

Participants

Reaction Steps

A solution of 2-Chloro-N-[3-(4-chloro-quinazolin-6-yl)-prop-2-ynyl]-acetamide (50 mg; 0.17mmol) and 3-methyl-4-phenoxyaniline (36 mg; 0.9 equiv.) in 1,2-dichloroethane (1 ml) and t-butanol (1 ml) was heated at 87° C. for 30 minutes. The mixture was then cooled to room temperature and diluted with ethyl acetate to further facilitate precipitation. The solution was then filtered to give the coupled product as a yellow powder (73 mg; 90%). 2.28 (3H, s), 4.10 (2H, s), 4.30 (2H, s), 6.93 (3H, d), 7.09 (1H, t), 7.34 (2H, t), 7.50-7.53 (1H, dd, J=2.6, 6 Hz), 7.63 (1H, d, J=2.4 Hz), 7.78 (I H, d, J=8 Hz), 8.06-8.08 (1H, dd, J=1.4, 7.2 Hz), 8.68 (1H, d, J=1.2 Hz), 8.75 (1H, s). Irms(M+): 457.0, 4.59.1; (M−): 455.7, 419.6

Provenance & Evidence