Triphenylphosphine → 2-(1-Azidoethyl)-1-phenyl-1H-imidazo[4,5-c]pyridine

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphoryl azide (0.50 g, 1.81 mmol) and diisopropyl azadicarboxylate (0.61 g, 3.01 mmol) were added to a stirred solution of 1-(1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)ethanol (0.36 g, 1.50 mmol) and triphenylphosphine (0.79 g, 3.01 mmol) in dioxane (15 mL) at 0° C. under nitrogen. After addition the mixture was stirred at 20° C. for 16 h. Additional diphenyl phosphoryl azide (0.25 g, 0.91 mmol), triphenylphosphine (0.40 g, 1.53 mmol) and diisopropyl azadicarboxylate (0.30 g, 1.48 mmol) were added and the resultant mixture stirred at 20° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound as an oil (0.60 g, contaminated with triphenylphosphine oxide). LCMS (method H): Rt 1.86 min, [M+H]+ 265

Provenance & Evidence