Sodium Carbonate → 4-bromo-7-(4-(pyren-1-yl)phenyl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate A (1.41 g, 4 mmol), pyrene-1-boronic acid (0.49 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.50 g, 0.43 mmol), sodium carbonate (2.12 g, 20 mmol) in water (10 mL), n-butanol (30 mL), and toluene (30 mL) was heated under argon at 110° C. for 5 hours. The reaction mixture was poured into water (200 mL), treated with 5 N NaOH (20 mL), stirred for 1 hour, and extracted with dichloromethane (2×200 mL). The extract was dried over anhydrous sodium carbonate, and the volatiles were removed under reduced pressure. The residue was chromatographed (silica gel, dichloromethane/tetrahydrofuran 9:10) to give 4-bromo-7-(4-(pyren-1-yl)phenyl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole (purity 90%, 650 mg, 53% yield) as yellow crystals. 1H NMR (400 MHz, CDCl3): δ 8.72 (m, 2H, pyridine), 8.31 (d, J=7.7 Hz, 1H, pyrene), 8.24 (dd, J=7.7 and 1.1 Hz, 1H, pyrene), 8.16-8.20 (m, 6H, pyrene and pyridine), 8.04 (t, J=7.7 Hz, 1H, pyrene), 8.00 (m, 2H, pyrene), 7.86 (d, J=7.7 Hz, 1H, benzotriazole), 7.86 (d, J=7.3 Hz, 1H, benzotriazole).

Provenance & Evidence