Sodium hydride → HCID 58335249, compound

Participants

Reaction Steps

To a suspension of sodium hydride (0.50 g, 12.38 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added a mixture of methyl hydroxyacetate (1.0 g, 11.25 mmol) and 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (3.4 g, 13.5 mmol) dropwise. After stirring for 5 hours, the reaction was quenched with iso-propanol/methanol solution. The reaction mixture was poured onto iced water and extracted with ether. The organic phase was dried over MgSO4, filtered and evaporated. The crude mixture was purified by silica gel column and eluted with ethyl acetate:petroleum ether (1:10) 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