2-Bromoethanol → HCID 59846150, compound

Participants

Reaction Steps

To a solution of 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzyl acetate (see preparation of 3-4 for this intermediate) (74 mg, 0.20 mmol) in dry DMF (1 mL) was added 60% sodium hydride in mineral oil (57 mg, 1.4 mmol). After 10 minutes 2-bromoethanol (50 μL, 0.71 mmol) was added to the reaction which was monitored over 24 hours by LC/MS. Two more portions of 2-bromoethanol were added during this period. The reaction was diluted with ethyl acetate and water. After stirring for 0.5 hour, the organic layer was isolated and washed with aqueous NaHCO3, dried (anhydrous Na2SO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with 30-100% ethyl acetate and then 0.25-1.5% methanol/ethyl acetate (sat'd with NH3) to give the title compound. 1H-NMR (500 MHz, CDCl3): δ 8.68 (1H, s), 7.47 (1H, d, J=7.8 Hz), 7.39 (2H, d, J=8 Hz), 7.27-7.31 (5H, m), 7.20-7.22 (2H, m), 6.89 (1H, d, J=7.5 Hz), 4.65 (2H, s) 4.19 (2H, t, J=5.3 Hz), 3.94 (2H, t, J=5.3 Hz) m/e (m+1): 373.2.

Provenance & Evidence