Morpholine → 4-(2-Fluoropyridin-3-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vessel was charged with 2-fluoro-3-iodopyridine (1.0211 g, 4.579 mmol), morpholine (0.3989 mL, 4.579 mmol), Pd2(dba)3 (0.2633 g, 0.2748 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.2232 g, 0.5495 mmol), and sodium t-butoxide (1.1363 g, 13.74 mmol) in toluene (15 mL). The reaction mixture was stirred and heated in a Discover® model microwave reactor (CEM, Matthews, N.C.) at 150° C. for 20 min (125 watts, Powermax™ feature on, ramp time 5 min). The solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (40M), eluting with a gradient of 1% to 5% methanol in DCM, to provide 4-(2-fluoropyridin-3-yl)morpholine.

Provenance & Evidence