Sodium hydride → HCID 58335249, compound

Participants

Reaction Steps

To a suspension of sodium hydride (0.50 g, 12.4 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added methyl hydroxyacetate (1.0 g, 11.3 mmol) and 2-bromo-6-(bromomethyl)pyridine (Example 8, Step 1) (3.4 g, 13.5 mmol). After stirring for 5 hours, the reaction was quenched with an isopropanol/methanol solution. The reaction mixture was poured into ice water and extracted with ether. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting material was purified by flash chromatography (silica, 10% ethyl acetate/hexanes) to afford the title compound. 1H NMR (400 MHz CDCl3): δ 7.55 (t, 1H), 7.48 (d, 1H), 7.39 (d, 1H), 4.71 (s, 2H), 4.22 (s, 2H), 3.77 (s, 3H).

Provenance & Evidence