Triphenylphosphine → N-Hydroxy-N-[1-[4-[4-(4-fluorophenyl)-5-(4-pyridyl)1H-imidazol-2-yl]phenyl]ethyl]urea

Participants

Reaction Conditions

Reaction Steps

To a mixture of a-Methyl-4-[4-(4-fluorophenyl)-5-(4-pyridyl)imidazol-2-yl]benzyl alcohol (0.25 g, 0.70 mmol), P(Ph)3 (0.46 g, 1.75 mmol) and N,O-bis(benzyloxycarbonyl)hydroxylamine (0.48 g, 1.75 mmol) in THF (15 mL) was added DEAD (0.28 mL, 1.75 mmol) at rt. The reaction mixture was stirred at this temperature for 3 h and the solvent evaporated. The residue was partially purified by flash chromatography eluting with 1% MeOH/CHCl3. Methanol (25 mL) was added to this material and the mixture was cooled to -78° C. Ammonia was bubbled in at this temperature for 15 min. The reaction mixture was warmed slowly to rt, stoppered and stirred at rt for 2 days. The solvent was evaporated and the residue was purified by flash chromatography eluting with a solvent gradient of 1-10% MeOH/CHCl3. The title compound was obtained as an off-white solid (0.43 g, 14%): FABMS (m/z): 418 (M+ +H).

Provenance & Evidence