Sodium Carbonate → HCID 86679905, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate A (purity 90%, 1.95 g, 5 mmol), sodium carbonate (2.69 g, 25 mmol), 4-(diphenylamino)phenylboronic acid (3.47 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0) (0.58 g, 0.5 mmol), water (20 mL), dioxane (80 mL), and toluene (10 mL) was heated under argon at 110° C. for 48 hours. The reaction mixture was poured into water (200 mL), diluted with dichloromethane (200 mL), treated with 2N NaOH (50 mL), stirred for 1 hour, and the dichloromethane layer was separated. The aqueous phase was washed with dichloromethane (200 mL). Both dichloromethane solutions were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography and recrystallization from ethyl acetate/ethanol (1:1) to give 4,7-bis(4-(N,N-diphenylamino)phenyl)-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole (Example 1), orange crystals, 1.71 g (50%). 1H NMR (400 MHz, CDCl3): δ 8.80 (m, 2H, pyridine), 8.34 (m, 2H, pyridine), 8.06 (d, J=8.7 Hz, 4H, p-phenylene), 7.67 (s, 2H, benzotriazole), 7.31 (m, 8H, Ph), 7.21 (m, 12H, p-phenylene and Ph), 7.08 (tt, J=7.3 and 2.2 Hz, 4H, Ph). UV-vis spectrum (dichloromethane): λmax=451 nm. Fluorimetry (dichloromethane): λmax=593 nm.

Provenance & Evidence