反应详情

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.

1. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
2. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
3. dry with materialthe combined organic solutions were dried (Na2SO4)
4. concentrationconcentrated
5. additionTo the resulting black residue were added CH2Cl2 and hexane
6. filtrationthe precipitated solid was filtered off
7. wash(washing with 1:1 CH2Cl2:hexane, followed by toluene)
8. concentrationThe filtrate was concentrated
9. custompurified by flash chromatography