5-Aminobenzene-1,3-dicarbonitrile → 3,5-Dicyanophenyl,3-(3,6-diphenyl-9-carbazolyl)phenylaniline

Participants

Reaction Steps

9.0 g of carbazole from step (2b) from Example 2 above and 2.7 g 5-aminoisophthalonitrile were mixed in 50 mL toluene in nitrogen filled glove box. 0.2 g Pd2DBA3 and 0.09 g tri-t-butylphosphinewere added followed quickly by 1.81 g t-BuONa. The mixture was heated briefly to reflux then held at 80° C. overnight in the glove box with vigorous stirring. After cooling the reaction was chromatographed on silica using a gradient of DCM:hexanes (1:4 to 4:1) to elute the product which upon concentration and addition of hexanes precipitated the desired product in 50% yield (˜4 g) with structure confirmed by 1-H nmr spectroscopy.

Provenance & Evidence