Sodium hydride → Ethyl 4-(6-bromopyridin-3-yl)-2-(methylsulfonyl)butanoate

Participants

Reaction Steps

A solution of ethyl(methylsulfonyl)acetate (1090 mg, 6.6 mmol, 1.0 equiv) in DMF (11 mL) was added dropwise to a mixture of 60% sodium hydride in mineral oil (315 mg, 7.9 mmol, 1.2 equiv) in DMF (11 mL) at 0° C. The reaction was warmed to room temperature and allowed to stir for 40 min. The reaction was cooled to 0° C. and a solution of 2-bromo-5-(2-iodoethyl)pyridine (2560 mg, 8.2 mmol, 1.3 equiv) in DMF (11 mL) was added dropwise, and the reaction was allowed to stir for 3 days. Saturated aqueous ammonium chloride solution (30 mL) was added, and the mixture was extracted with ethyl acetate (3×70 mL). The combined organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (7:3 heptane/ethyl acetate) to provide the title compound as a white solid (1628 mg, 71%). MS (LCMS) m/z 352.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29-1.35 (m, 3H) 2.30-2.44 (m, 2H) 2.62-2.78 (m, 2H) 3.00 (s, 3H) 3.71 (dd, J=9.37, 4.68 Hz, 1H) 4.21-4.35 (m, 2H) 7.36-7.46 (m, 2H) 8.19 (d, J=1.56 Hz, 1H).

Provenance & Evidence