Methyl iodide → HCID 90010262, compound

Participants

Reaction Steps

Step-2: Ethyl 3-(5-bromo-6-ethylpyridin-3-yl)-2,2-dimethyl-3-oxopropanoate: To a 0° C. cooled and stirred suspension of sodium hydride (60% dispersion inoil, 120 mg, 5 mmol), in DMF (3 mL) was added ethyl 3-(5-bromo-6-ethylpyridin-3-yl)-3-oxopropanoate (0.5 g, 1.66 mmol) in DMF (7 mL) over a period of 15 min. The reaction mixture was then stirred for 15 min at the same temperature and Iodomethane (365 μl, 5.83 mmol) was added to the above mixture. The resulting mixture was then warmed to room temperature and stirred for 3 h. The reaction mixture was diluted with water (30 mL) followed by ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 300 mg (54%) of the title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.77 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.0 Hz, 1H), 4.12 (q, J=7.0 Hz, 2H), 2.96 (q, J=7.0 Hz, 2H), 1.46 (s, 6H), 1.25 (t, J=7.0 Hz, 3H), 1.03 (t, J=7.0 Hz, 3H); ESI-MS (m/z) 328, 330 [(MH+, Br79,81].

Provenance & Evidence