Potassium Carbonate → [7-(2,6-Dimethoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine

Participants

Reaction Steps

To a solution of (7-Bromo-5-methyl-benzo[1,2,4]triazin-3-yl)-phenyl-amine (10 mg, 0.032 mmol) dissolved in 2 ml N,N-Dimethylacetamide in a 20 ml vial, 2,6-dimethoxy-phenylboronic acid (23 mg, 0.126 mmol) dissolved in 1 ml ethanol and potassium carbonate (6.4 mg, 0.06 mmol) dissolved in 1 ml water were added. Triphenylphosphine (1 mg, 0.0038 mmol) and tris(dibenzylideneacetone) dipalladium (0) (1 mg, 1.09 umol) were added to the mixture. The mixture was reflux overnight. The crude product was filtered and purified by preparative HPLC. 5 mg [7-(2,6-Dimethoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-phenyl-amine was isolated. Yield: 42.4%; ESI-MS: [M+H]+, 373; 1H NMR (CDCl3): δ 2.72 (s, 3 H), 3.78 (s, 6 H), 6.70 (d, J=8.4 Hz, 2 H), 7.13 (m, 1 H), 7.35 (t, J=8.38 Hz, 1 H), 7.44 (m, 2 H), 7.89 (m, 1 H), 7.92 (dd, J1=8.78 Hz, J2=2.02 Hz, 2 H), 8.18 (d, J=2.02 Hz, 1 H).

Provenance & Evidence