3-Fluorophenol → 2-((3-fluorophenoxy)methyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

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Reaction Steps

2-(Hydroxymethyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (270 mg, 0.9 mmol) from above and 3 equiv of 3-fluorophenol was dissolved in THF (10 mL). To this mixture was added polystyrene bound-PPh3 (3 equiv) and diisopropylazodicarboxylate (3 equiv) in THF (2 mL) dropwise. The mixture was allowed to warm to RT and stirred for 6 h. The residue was loaded directly onto a silica and eluted with EtOAc/hexanes to give the compound (310 mg, 88%). LC-MS (M+H)=393.2.

Provenance & Evidence