Potassium Phosphate, Tribasic → 2-(4-phenylpyridin-2-yl)-9H-carbazole

Participants

Reaction Conditions

Reaction Steps

To a three-necked flask equipped with a magnetic stir bar was added 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (682 mg, 2.32 mmol, 1.1 eq), 2-chloro-4-phenylpyridine (400 mg, 2.11 mmol, 1.0 eq), Pd2(dba)3 (21 mg, 0.023 mmol, 0.01 eq), PCy3 (14 mg, 0.051 mmol, 0.024 eq) and K3PO4 (761 mg, 3.59 mmol, 1.7 eq). Then the flask was evacuated and back-filled with nitrogen, and the evacuation and back-fill procedure was repeated twice. Then solvent dioxane (8 mL) and water (3.8 mL) were added under the protection of nitrogen. The mixture was stirred in an oil bath at a temperature of 100-105° C. for 16 hours. Then the mixture was cooled to ambient temperature and diluted with ethyl acetate. The organic layer was separated and dried over sodium sulfate, and filtered, the filtrate was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (5:1-3:1-2:1) as an eluent to obtain the desired product, 2-(4-phenylpyridin-2-yl)-9H-carbazole, as a brown solid (675 mg in 99% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.20 (t, J=7.6 Hz, 1H), 7.41-7.45 (m, 1H), 7.51-7.61 (m, 4H), 7.68 (dd, J=4.8, 1.2 Hz, 1H), 7.96-7.98 (m, 2H), 8.05 (dd, J=7.6, 1.6 Hz, 1H), 8.18 (d, J=7.6 Hz, 1H), 8.24 (d, J=8.0 Hz, 1H), 8.31 (s, 1H), 8.35 (d, J=0.4 Hz, 1H), 8.77 (d, J=5.2 Hz, 1H), 11.37 (s, 1H).

Provenance & Evidence