Sodium Carbonate → 7-(2-Chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine

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7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (3.35 mmol, 1.0 equiv), 2-chloro-5-nitrophenyl-boronic acid (5.02 mmol, 1.5 equiv), Pd(PPh3)4 (0.335 mmol, 0.1 equiv), and Na2CO3 (13.4 mmol, 4.0 equiv) were dissolved in a mixture of DME/EtOH/H2O (4:1:1 v/v/v) and refluxed at 100° C. for 18 h. The reaction was diluted with 50 mL DCM and filtered. The precipitate was suspended in water to remove excess Na2CO3 and filtered again with a final Et2O wash to remove water. The crude precipitate gave 7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, as a dark green solid (1.0 g, 94% yield). Rf=0.55 MS (ES+) m/z=316 LC retention time 2.96 min.

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