2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631368, compound

Participants

Reaction Conditions

Reaction Steps

A screw-cap vial was charged with 4-chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinoline (50 mg, 0.16 mmol), 2,5-dimorpholinopyridin-3-amine (43.4 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium (0) (15.0 mg, 0.016 mmol), XPhos (15.6 mg, 0.033 mmol), sodium tert-butoxide (47.3 mg, 0.49 mmol), and toluene (1.5 mL). The mixture was stirred at 105° C. for 2 h, then cond. The resulting residue was partitioned between DCM and water, and the organic layer was dried over magnesium sulfate and cond. The crude material was purified by recrystallization in MeOH, affording N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinolin-4-amine. Mass Spectrum (ESI) m/e=533.0 (M+1). 1H NMR (400 MHz, chloroform-d) δ ppm 8.64 (1H, d, J=1.8 Hz), 8.57 (1H, d, J=1.6 Hz), 7.83 (1H, s), 7.78 (1H, br. s.), 7.67 (1H, d, J=2.5 Hz), 7.63 (1H, d, J=9.4 Hz), 6.98-7.09 (1H, m), 6.32-6.42 (1H, m), 3.91 (4H, br. s.), 3.77-3.86 (4H, m), 3.09-3.41 (4H, br. s.), 2.99-3.09 (4H, m), 2.48 (3H, s), 2.17 (3H, s).

Provenance & Evidence