Methyl iodide → HCID 57744890, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate(same as methyl 5-bromo-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate described in Step 2 of Example 34) (996 mg, 3.00 mmol), potassium carbonate (829 mg, 6.00 mmol), DMF (6 mL) and methyl iodide (0.225 mL, 3.60 mmol) was stirred at 60° C. for 4 h. Then, the mixture was poured into saturated aqueous NaHCO3 (100 mL). Extraction with EtOAc (100 mL), washing with saturated aqueous NaHCO3 and brine, drying over MgSO4, filtration and concentration under reduced pressure gave brown oil. This residue was mixed with potassium carbonate (415 mg, 3.00 mmol), MeOH (20 mL) and water (10 mL). The mixture was stirred overnight at room temperature. Then, the mixture was poured into saturated aqueous NaHCO3 (100 mL). Extraction with EtOAc (100 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave brown oil. This residue was purified by column chromatography (Purif, silica gel, hexane to 70:30 hexane/EtOAc) to afford the title compound (674 mg, 90%) as a white solid:

Provenance & Evidence