Nitrogen → N-[3-(2,2-dipyridin-3-ylethyl)pyridin-2-yl]benzene-1,2-diamine

Participants

Reaction Steps

To a solution of 2-chloro-3-(2,2-dipyridin-3-ylethyl)pyridine in 160 mL toluene was added phenylenediamine (8.41 g), tris(dibenzylideneacetone)-dipalladium(0) (356 mg), 1,1-bis(diphenylphosphino)ferrocene (431 mg), and sodium tert-butoxide (2.24 g) under N2. The reaction was heated at 100 C under a stream of N2 for 14 h, then partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (3×), and the combined organic solutions were dried (Na2SO4) and concentrated. To the resulting black residue were added CH2Cl2 and hexane, and the precipitated solid was filtered off (washing with 1:1 CH2Cl2:hexane, followed by toluene). The filtrate was concentrated and purified by flash chromatography to give 4.1 g of N-[3-(2,2-dipyridin-3-ylethyl)pyridin-2-yl]benzene-1,2-diamine as a grey solid.

Provenance & Evidence