1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59829664, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-{5-[(dimethylamino)methyl]-2-furyl}ethanol (2.18 mmol) in toluene (13.5 mL) and dimethylformamide (2.7 mL) at 0° C. was added diphenyl phosphoryl azide (5.46 mmol, 2.5 eq.) followed by dropwise addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (5.46 mmol, 2.5 eq.). The reaction mixture was stirred 5 min at 0° C. then warmed to room temperature and stirred 16 h. The mixture was next diluted with saturated aqueous lithium bromide solution (25 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to a dark brown syrup that was purified by column chromatography using 30% acetone/dichloromethane to give the product as a brown syrup (1.65 mmol, 76%). MS (ESI) m/z 462.4; HRMS: calcd for C25H24ClN5O2+H+, 462.16913; found (ESI, [M+H]+ Obs'd), 462.1693.

Provenance & Evidence