Methyl iodide → HCID 71281843, compound

Participants

Reaction Steps

To solution of ethyl 2-bromo-6H-thieno[2,3-b]pyrrole-5-carboxylate (6.35 g, 23.16 mmol) in DMF (80 mL) at 0° C. was added NaH (60%, 1.54 g, 38.50 mmol) in portions. Reaction mixture was stirred at 0° C. for 15 min before MeI (2.90 mL, 46.58 mmol) was added. It was then allowed to warm to room temperature and was stirred 1.5 h. Reaction mixture was cooled to 0° C. and was quenched with solution of NH4Cl (aqueous saturated, 50 mL). It was then diluted with H2O (˜200 mL) and product was extracted with EtOAc (3×100 mL). Combined organics were washed with NaCl (aqueous saturated, 80 mL) and dried over Na2SO4. After concentration of the solvent residue was purified by column chromatography (EtOAc/hexanes, 0-10% gradient) to yield ethyl 2-bromo-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxylate (5.47 g) in 82% yield.

Provenance & Evidence