Potassium Carbonate → 7-(2,6-dimethylphenyl)-5-methyl-N-phenylbenzo[e][1,2,4]triazin-3-amine

Participants

Reaction Steps

To a solution of (7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine (60 mg, 0.19 mmol) dissolved in 3 ml N,N-Dimethylacetamide in a 20 ml vial, 2,6-dimethyl-phenylboronic acid (114 mg, 0.76 mmol) dissolved in 2 ml ethanol and potassium carbonate (31 mg, 0.3 mmol) dissolved in 1 ml water were added. Triphenylphosphine (4.5 mg, 0.0171 mmol) and tris(dibenzylideneacetone) dipalladium (0) (4.5 mg, 4.9 umol) were added to the mixture. The mixture was reflux overnight. The crude product was filtered and purified by preparative HPLC. 30 mg [7-(2,6-Dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 46%; ESI-MS: [M+H]+, 341; 1H NMR (DMSO-d6): δ 2.05 (s, 6 H), 2.67(s, 3H), 7.07(t, J=7.33 Hz, 1 H), 7.17–7.24 (m, 3 H), 7.41 (t, J=7.56 Hz, 2 H), 7.62 (d, J=1.49 Hz, 1 H), 7.93 (d, J=1.49 Hz, 1 H), 8.05 (d, J=7.72 Hz, 1H).

Provenance & Evidence