8-Bromoquinoline → 7-(2,6-dimethylphenyl)-5-methyl-N-(quinolin-8-yl)benzo[e][1,2,4]triazin-3-amine

Participants

Reaction Steps

About 100 mg (0.4 mmol) of 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine and about 158 mg (0.8 mmol) of 8-bromo-quinoline were dissolved in about 10 ml toluene. About 17 mg (0.018 mmol) of Pd(dba)3, about 17 mg (0.027 mmol) of BINAP, and about 50 mg (0.226 mmol) of KOt-Bu were added to the solution. The mixture was kept at about 100° C. for about 24 hours under argon. The crude product was purified by preparative HPLC. About 50 mg [7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-quinolin-8-yl-amine (product having formula (XII)) was isolated. Yield: about 33.8%; ESI-MS: [M+H]+, 392; 1H NMR (DMSO-d6): δ 2.07 (s, 6 H), 2.79 (s, 3H), 7.19 (d, J=7.4 Hz, 2 H), 7.25 (m, 1 H), 7.71-7.79 (m, 4 H), 8.04 (s, 1 H), 8.50 (d, J=8.3 Hz, 1 H), 9.05 (m, 2 H).

Provenance & Evidence