Morpholine → HCID 59631135, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine (35.5 mg, 0.07 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (7.1 mg, 0.015 mmol), tris(dibenzylideneacetone)dipalladium (0) (6.9 mg, 7.54 μmol), morpholine (0.05 mL, 0.57 mmol), and sodium tert-butoxide (20.7 mg, 0.215 mmol) in dry toluene (2.0 mL) was degassed by nitrogen. The mixture was heated to 100° C. After 21.5 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration and concentration, the light orange film was purified by HPLC 10-60% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution. The desired fractions were concentrated then diluted with EtOAc. After washing twice with satd aq. sodium bicarbonate solution and once with brine, the solvent was removed under reduced pressure to yield a white solid as N-(2-(3,6-dihydro-2H-pyran-4-yl)-5-(4-morpholinyl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. Mass Spectrum (pos.) m/e: 516.3 (M+1)+.

Provenance & Evidence