Morpholine → HCID 59631587, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-bromo-5′-fluoro-2′-methoxy-2,4′-bipyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (50.2 mg, 0.091 mmol), morpholine (0.03 mL, 0.34 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (9.1 mg, 0.019 mmol), tris(dibenzylideneacetone)dipalladium (0) (8.5 mg, 9.28 μmol), and sodium tert-butoxide (26.7 mg, 0.28 mmol) in dry Toluene (3 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 organic layer was combined and dried over anhydrous magnesium sulfate. After filtration and concentration, the light orange film was purified with HPLC 10-60% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution. The impure fractions were further purified with SFC chromatography to afford a white solid as 5,7-difluoro-N-(5′-fluoro-2′-methoxy-5-morpholino-2,4′-bipyridin-3-yl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.68 (1H, br. s.), 8.10 (2H, t, J=2.0 Hz), 7.96 (2H, m), 7.66 (1H, m.), 7.38 (1H, m), 7.07 (2H, m), 6.61 (1H, m), 3.96 (3H, s), 3.91 (4H, m), 3.30 (4H, m), 2.17 (3H, s). Mass Spectrum (pos.) m/e: 559.2 (M+1).

Provenance & Evidence