Nitrogen → 2-Pyridyl-2-quinolylamine

Beteiligte Stoffe

Reaktionsschritte

To a 250-mL round-bottom flask were added 2-aminopyridine (2.30 g, 24.4 mmol), 2-chloroquinoline (4.0 g, 24.4 mmol), sodium tert-butoxide (3.29 g, 34.2 mmol), palladium (II) acetate (0.22 g, 0.98 mmol), bis(2-diphenylphosphinophenyl)ether (0.49 g, 0.91 mmol), and toluene (100 mL sparged with N2). The reaction mixture was heated at 105° C. for 18 h under an atm of N2. The reaction mixture was diluted with ether and THF, and washed with water. This solution was passed through a pad of celite to remove insoluble particles. The organic layer was dried over MgSO4. The crude product was purified by column chromatography eluting with 90:10 CH2Cl2/CH3CN. 2-Pyridyl-2-quinolylamine was isolated as an olive powder (4.66 g, 86%). Results of 1H NMR spectroscopy are consistent with the product. 1H NMR (300 MHz, CDCl3): δ 6.93 (m, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.35 (t, J=7.4 Hz, 1H), 7.62 (m, 1H), 7.70 (m, 2H), 7.86 (d, J=8.4 Hz, 1H), 8.0 (m, 2H), 8.31 (m, 1H), 8.38 (d, J=8.5 Hz, 1H).

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