4-Methoxypiperidine → HCID 50906993, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of N-(5-bromo-2-morpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.057 g, 0.110 mmol), 4-methoxypiperidine (commercially available from Oakwood Products, Inc.) (0.035 g, 0.30 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.013 g, 0.014 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (0.012 g, 0.026 mmol), and sodium tert-butoxide (0.056 g, 0.58 mmol) in dry toluene (3.0 mL) was purged three times with argon and placed under vacuum three times, then 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 DCM:MeOH (95:5), the organics were combined and dried over anhydrous magnesium sulfate. After filtration and concentration the residue was purified on basic alumina (0-35% EtOAc in hexanes) to afford a light yellow solid as 5,7-difluoro-N-(5-(4-methoxy-1-piperidinyl)-2-(4-morpholinyl)-3-pyridinyl)-3-methyl-2-(2-pyridinyl)-4-quinolinamine. Mass Spectrum ESI (pos.) m/e: 547.2 (M+H)+.

Provenance & Evidence