Methyl iodide → HCID 71203617, compound

Participants

Reaction Steps

A solution of methyl 5-(3-bromo-4-methoxyphenyl)-4-methyl-1H-pyrrole-2-carboxylate (prepared according to the procedure reported in J. Org. Chem., 2009, 74(2), 903-905, Org. Lett., 2007, Vol. 9, 25, 5191-5194, 1.40 g, 4.32 mmol) in DMF (3 ml) was added to a solution of sodium hydride (0.21 g 60% in paraffin oil, 4.75 mmol) in DMF (2 ml) at 0° C. under stirring. Methyl iodide (0.67 g, 0.29 ml, 4.75 mmol) was then added to the reaction mixture. The reaction mixture was stirred at room temperature for 45 minutes. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with water (5 ml) and then extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product. The crude product was further purified by flash column chromatography using 20% ethyl acetate in hexanes as an eluent to obtain the title compound 10a (1.25 g, 85%).

Provenance & Evidence