1-Methylimidazole → 9-(4-methylpyridin-2-yl)-2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole

Participants

Reaction Conditions

Reaction Steps

To a dry pressure vessel equipped with a magnetic stir bar was added 2-(3-(quinolin-2-yl)phenoxy)-9H-carbazole (773 mg, 2.0 mmol, 1.0 eq), CuI (76 mg, 0.4 mmol, 0.2 eq), and K2CO3 (553 mg, 4.0 mmol, 2.0 eq). The vessel was evacuated and back-filled with nitrogen. The evacuation and back-fill procedure was repeated twice. Then 2-bromo-4-methylpyridine (1032 mg, 6.0 mmol, 3.0 eq), 1-methyl-1H-imidazole (158 uL, 2.0 mmol, 1.0 eq) and solvent toluene (32 mL) were added under nitrogen. After bubbling with nitrogen for 25 minutes, the mixture was stirred in an oil bath at a temperature of 120° C. for three days, and cooled to ambient temperature. The solid was filtered off and washed with ethyl acetate. The filtrate was concentrated and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1-3:1) as an eluent to afford the desired product Ligand ON11Me as a sticky liquid (955 mg) in 99%. 1H NMR (DMSO-d6, 400 MHz): δ 2.38 (s, 3H), 7.09 (dd, J=8.4, 2.4 Hz, 1H), 7.18 (dd, J=8.4, 2.4 Hz, 1H), 7.25 (d, J=5.2 Hz, 1H), 7.32 (t, J=7.6 Hz, 1H), 7.43 (t, J=7.6 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.54-7.60 (m, 3H), 7.72-7.77 (m, 2H), 7.97-8.04 (m, 4H), 8.13 (d, J=9.2 Hz, 1H), 8.21 (d, J=7.6 Hz, 1H), 8.27 (d, J=8.0 Hz, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.49 (d, J=4.8 Hz, 1H).

Provenance & Evidence