Sodium t-butoxide → HCID 59631267, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluoro-5-morpholinopyridin-3-amine (0.12 g, 0.60 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.261 g, 0.90 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.055 g, 0.060 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (0.058 g, 0.121 mmol), and sodium tert-butoxide (0.176 g, 1.83 mmol) in dry toluene (5.0 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 21.5 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organics were combined and dried over anhydrous magnesium sulfate. After filtration and concentration the residue was purified on basic alumina (0-60% EtOAc in hexanes) to afford an light yellow solid as 5,7-difluoro-N-(2-fluoro-5-(4-morpholinyl)-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (500 MHz, CDCl3) δ ppm 8.71 (1H, d, J=4.6 Hz), 7.93 (2H, m), 7.70 (1H, m), 7.42 (1H, d, J=2.7 Hz), 7.32 (1H, m), 7.15 (1H, m), 7.01 (1H, m), 6.58 (1H, d, J=7.1 Hz), 3.88 (4H, m), 3.16 (4H, m), 2.23 (3H, s). Mass Spectrum ESI (pos.) m/e: 452.2 (M+H)+.

Provenance & Evidence